- Application of tert-Butyl Disulfide-Protected Amino Acids for the Fmoc Solid-Phase Synthesis of Lactam Cyclic Peptides under Mild Metal-Free Conditions
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Lactam cyclic peptides are a class of interesting and pharmaceutically active molecules, but their previous syntheses have required the use of heavy metals and/or forcing conditions. Here, we describe the efficient application of the previously reported tert-butyl disulfide-protected amino acids and their use in the efficient, solid-phase synthesis of a series of lactam cyclic peptides under mild, metal-free conditions.
- Chen, Junyou,Cui, Tingting,Sun, Shuaishuai,Guo, Yanyan,Chen, Jingnan,Wang, Jun,Bierer, Donald,Li, Yi-Ming
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p. 8610 - 8619
(2021/07/19)
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- Activity-Based Genetically Encoded Fluorescent and Luminescent Probes for Detecting Formaldehyde in Living Cells
-
Formaldehyde (FA) is endogenously produced in living systems through a variety of biological processes and has been implicated in many pathological conditions. Detection tools for biological FA are therefore of great interest. Reported here are novel activity-based genetically encoded fluorescent and luminescent probes for detecting FA in aqueous solutions and living mammalian cells. A FA-reactive lysine analogue, PrAK, was site-specifically incorporated into the essential lysine sites of enhanced green fluorescent protein (EGFP) and firefly luciferase (fLuc) to afford fluorescent and luminescent FA probes, respectively. FA selectively reacts with PrAK residues on EGFP and fLuc through a 2-aza-Cope rearrangement, resulting in fluorescence and luminescence turn-on responses, respectively, to FA selectively over potentially interfering reactive species in aqueous buffer. Moreover, the genetically encoded probes are capable of visualizing FA at physiologically relevant levels in living mammalian cells by fluorescence and luminescence imaging, demonstrating their potential as new tools to explore FA biology.
- Du, Yimeng,Li, Manjia,Peng, Tao,Xiang, Zheng,Zhang, Dong,Zhang, Yuqing
-
supporting information
p. 16352 - 16356
(2020/07/25)
-
- Light-controlled self-assembly of a dithienylethene bolaamphiphile in water
-
The self-assembly of bolaamphiphiles comprised of a central photochromic dithienylethene (DTE) chromophore was investigated in aqueous media. Irradiation at 254 nm induced a conversion from the open to closed states of the DTE chromophores. Whereas, in water, irradiation produced a photostationary state of 20 : 80 (open/closed), in methanol the ratio improved to 10 : 90 (open/closed). The open → closed transition was accompanied by the formation of 1D nanofibers during incubation in darkness. This journal is
- Creemer, Cassidy,Kilic, Haydar,Lee, Kwang Soo,Parquette, Jon R.,Saracoglu, Nurullah
-
supporting information
p. 8846 - 8849
(2020/07/21)
-
- The impact of metal coordination on the assembly of bis(indolyl)methane-naphthalene-diimide amphiphiles
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The self-assembly and coordination of amphiphiles comprised of naphthalenediimide (NDI) and bis(indolyl)methane (BIM) chromophores were investigated as a function of pH and metal. As observed by TEM, SEM and AFM imaging, the self-assembly of NDI-BIM 1 pro
- Bayindir, Sinan,Lee, Kwang Soo,Parquette, Jon R.,Saracoglu, Nurullah
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supporting information
p. 13685 - 13692
(2020/10/26)
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- NOVEL CXCR4 ANTAGONISTS WITH AMINO ACID SKELETON, PREPARATION THEREFOR AND BIOMEDICAL USE THEREOF
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The present invention provides a compound represented by formula (I), or a pharmaceutically acceptable salt or prodrug thereof.
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Paragraph 0081
(2020/09/09)
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- Microwave-assisted synthesis of: Meso-carboxyalkyl-BODIPYs and an application to fluorescence imaging
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In this study, a significantly improved method for the synthesis of modular meso-BODIPY (boron dipyrromethene) derivatives possessing a free carboxylic acid group (which was subsequently coupled to peptides), is disclosed. This method provides a vastly efficient synthetic route with a > threefold higher overall yield than other reports. The resultant meso-BODIPY acid allowed for further easy incorporation into peptides. The meso-BODIPY peptides showed absorption maxima from 495-498 nm and emission maxima from 504-506 nm, molar absorptivity coefficients from 33383-80434 M-1 cm-1 and fluorescent quantum yields from 0.508-0.849. The meso-BODIPY-c(RGDyK) peptide was evaluated for plasma stability and (proved to be durable even up to 4 h) was then assessed for its fluorescence imaging applicability in vivo and ex vivo. The optical imaging in vivo was limited due to autofluorescence, however, the ex vivo tissue analysis displayed BODIPY-c(RGDyK) internalization and cancer detection thereby making it a novel tumor-integrin associated fluorescent probe while displaying the lack of interference the dye has on the properties of this ligand to bind the receptor. This journal is
- Driver, Cathryn H. S.,Ebenhan, Thomas,Govender, Thavendran,Kruger, Hendrick G.,Maguire, Glenn. E. M.,Mhlongo, Neliswa Z.,Naicker, Tricia
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supporting information
p. 7876 - 7883
(2020/11/02)
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- Highly potent and selective aryl-1,2,3-triazolyl benzylpiperidine inhibitors toward butyrylcholinesterase in Alzheimer's disease
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Acetylcholinesterase (AChE) is the key enzyme targeted in Alzheimer's disease (AD) therapy, nevertheless butyrylcholinesterase (BuChE) has been drawing attention due to its role in the disease progression. Thus, we aimed to synthesize novel cholinesterases inhibitors considering structural differences in their peripheral site, exploiting a moiety replacement approach based on the potent and selective hAChE drug donepezil. Hence, two small series of N-benzylpiperidine based compounds have successfully been synthesized as novel potent and selective hBuChE inhibitors. The most promising compounds (9 and 11) were not cytotoxic and their kinetic study accounted for dual binding site mode of interaction, which is in agreement with further docking and molecular dynamics studies. Therefore, this study demonstrates how our strategy enabled the discovery of novel promising and privileged structures. Remarkably, compound 11 proved to be one of the most potent (0.17 nM) and selective (>58,000-fold) hBuChE inhibitor ever reported.
- de Andrade, Peterson,Mantoani, Susimaire P.,Gon?alves Nunes, Paulo Sérgio,Magadán, Carlos Roca,Pérez, Concepción,Xavier, Danilo Jord?o,Hojo, Elza Tiemi Sakamoto,Campillo, Nuria E.,Martínez, Ana,Carvalho, Ivone
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p. 931 - 943
(2019/02/14)
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- Development of a hybrid peptide dendrimer micellar carrier system and its application in the reformulation of a hydrophobic therapeutic agent derived from traditional Chinese medicine
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The discovery that a cane toad poison-derived steroid, bufalin can significantly impact cancer cell proliferation supports its potential use in cancer therapy. However, its poor aqueous solubility and tissue deposition characteristics hamper its broader application as an anticancer therapeutic agent in its own right. To address this we developed an amphiphilic dendrimer-based delivery system, which self-assembles into discrete micelles in an aqueous environment. The bufalin-micelle inclusion complex was prepared by the co-precipitation method and their presence was confirmed by dynamic light scattering (DLS), zeta potential and differential scanning calorimetry (DSC) and transmission electron microscopy (TEM) measurements. The self-assembled bufalin-containing micelles were found to form at/above the dendrimer concentration of 105.38 μmol L-1, and showed a more than threefold increase in the aqueous solubility (142.9 μg mL-1) of bufalin, when compared with a saturated bufalin aqueous solution (42.4 μg mL-1), and two non-assembling peptides of similar composition (79.3 and 62.5 μg mL-1 respectively).
- Jing, Jing,Tupally, Karnaker R.,Kokil, Ganesh R.,Qu, Zhi,Chen, Sibao,Parekh, Harendra S.
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p. 2458 - 2463
(2019/02/01)
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- NEW TARGETED CYTOTOXIC RATJADONE DERIVATIVES AND CONJUGATES THEREOF
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The present invention is directed to novel natural product-derived ratjadone-based compounds useful as payloads (or toxins) in drug-conjugates constructs with cell target binding moieties (CTBM) and payload-linker compounds useful in connection with drug conjugates. The present invention further relates to new ratjadone compositions including the aforementioned payloads, payload-linkers and drug conjugates, and methods for using these payloads, payload-linkers and drug conjugates, to treat pathological conditions including cancer, inflammatory and infectious diseases.
- -
-
Paragraph 00224
(2019/02/25)
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- Design, Synthesis, and Evaluation of Lipopeptide Conjugates of Mercaptoundecahydrododecaborate for Boron Neutron Capture Therapy
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We developed new 10B carriers for boron neutron capture therapy (BNCT) that can effectively transport and accumulate boron clusters into cells. These carriers consist of a lipopeptide, mercaptoundecahydrododecaborate (BSH), and a disulfide linker. The carriers were conceived according to the structure of pepducin, a membrane-penetrating lipopeptide targeting protease-activated receptor 1 (PAR1). To improve the membrane permeability of BSH, the structure was optimized using various lipopeptides possessing different peptides and lipid moieties. These synthesized lipopeptides were conjugated with BSH and evaluated for intracellular uptake using T98G glioblastoma cells. Among them, the most effectively incorporated and accumulated in the cells was compound 5 a, which contains a peptide of 13 residues derived from the intracellular third loop of PAR1 and a palmitoyl group. For further improvement of 10B accumulation in cells, the introduction of an amine linker was investigated; intracellular uptake similar to that of 5 a was observed for compound 14, which has a piperazine linker. Both compounds 5 a and 14 showed a stronger radiosensitizing effect than BSH along on T98G cells under mixed-neutron beam irradiation. The results demonstrate that lipopeptide conjugation is effective for enhancing intracellular delivery and accumulation of BSH and improving the cytotoxic effect of BNCT.
- Isono, Aoi,Tsuji, Mieko,Sanada, Yu,Matsushita, Akari,Masunaga, Shinichiro,Hirayama, Tasuku,Nagasawa, Hideko
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supporting information
(2019/03/07)
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- Supported Catalytically Active Supramolecular Hydrogels for Continuous Flow Chemistry
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Inspired by biology, one current goal in supramolecular chemistry is to control the emergence of new functionalities arising from the self-assembly of molecules. In particular, some peptides can self-assemble and generate exceptionally catalytically active fibrous networks able to underpin hydrogels. Unfortunately, the mechanical fragility of these materials is incompatible with process developments, relaying this exciting field to academic curiosity. Here, we show that this drawback can be circumvented by enzyme-assisted self-assembly of peptides initiated at the walls of a supporting porous material. We applied this strategy to grow an esterase-like catalytically active supramolecular hydrogel (CASH) in an open-cell polymer foam, filling the whole interior space. Our supported CASH material is highly efficient towards inactivated esters and enables the kinetic resolution of racemates. This hybrid material is robust enough to be used in continuous flow reactors, and is reusable and stable over months.
- Rodon Fores, Jennifer,Criado-Gonzalez, Miryam,Chaumont, Alain,Carvalho, Alain,Blanck, Christian,Schmutz, Marc,Serra, Christophe A.,Boulmedais,Schaaf, Pierre,Jierry, Lo?c
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supporting information
p. 18817 - 18822
(2019/11/16)
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- Method for cross-linking peptides
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The present invention relates to a method for cross-linking peptides using an activated furan-moiety. In particular, the present invention provides a method for cross-linking peptides comprising the steps of: a) providing a composition comprising furan-pe
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- Synthesis of Novel Protected Nα(ω-Drug) Amino Acid Building Units for Facile Preparation of Anticancer Drug-Conjugates
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Abstract: We report about the preparation of novel protected Nα(ω-drug) amino acid building units and their straightforward incorporation in solid phase synthesis for the preparation of peptide-drug conjugates. These building units were synthesized applying various coupling methods between anticancer drugs and the side chains of different Nα protected amino acids. Subsequent incorporation of these amino acid-drug motifs into linear and cyclic integrin RGD and NGR containing ligands enabled a non-linear/divergent synthetic pathway of medicinally potential peptide-drug conjugates. The synthetic routes reported in this work are both general and applicable, and significantly expand the scope of the conjugation capabilities for peptide drug conjugates. For the preliminary in vitro evaluation of the novel peptide-drug conjugates reported herein, selective cytotoxicity of two representatives—one linear and one cyclic RGD—camptothecin conjugates were evaluated on αvβ3 integrin overexpressed cancer cell lines. Graphical Abstract: [Figure not available: see fulltext.]
- Gilad,Waintraub,Albeck,Gellerman
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p. 301 - 316
(2016/08/13)
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- Reagents and methods for sirtuin capture
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The invention provides a method of preparing a sirtuin complex, a method for detecting a sirtuin in a sample, and a method of screening for compounds which inhibit the deacetylase activity of a sirtuin. The method includes (a) providing a sirtuin substrate having the formula: (b) providing NAD+ or an NAD+ analog having the formula: and (c) providing a sirtuin, wherein R1-R4, A1, A2, and n are as defined herein.
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- Solid-phase synthesis of peptide conjugates derived from the antimicrobial cyclic decapeptide BPC194
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The solid-phase conjugation of the antimicrobial peptide c(KKLKKFKKLQ) (BPC194) to a linear or cyclic sequence through a 1,2,3-triazole ring is described. Cyclic alkynylpeptidyl resins derived from BPC194 were treated with azidopeptides derived from the antimicrobial peptide BP100 or from the bacteriocin iturin A. The cyclic alkynyl-peptidyl resins incorporated at the 3-position a propargylglycine, a glutamic acid residue derivatized with propargylamine or a lysine bearing a propioloyl group. The reactions of the cyclic alkynyl resins with the BP100-derived azidopeptides depended on the length and the sequence of the azidopeptides. The reactions were performed by treatment of the alkynyl resin with CuI and ascorbic acid, and required the presence of piperidine/DMF or DIEA in 2,6-lutidine/DMF. The latter conditions also allowed the conjugation of the alkynyl-peptidyl resin bearing a propioloyl lysine to a linear or cyclic azidopeptide derived from the cyclic moiety of iturin A.
- Vil, Slvia,Badosa, Esther,Montesinos, Emilio,Feliu, Lidia,Planas, Marta
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p. 1117 - 1129
(2015/02/19)
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- Modular Imaging Agents Containing Amino Acids and Peptides
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Targeting agents are derived from coupling together formed imaging amino acids or formed multi-modal, multi-chelating metal, multi-dye imaging agents, or combinations of these, that may be conjugated directly, or activated, or attached to linkers to which targeting groups, such as peptides, proteins, antibodies, aptamers, or small molecule inhibitors, may be conjugated in the final steps of the synthesis to form a wide variety of TMIAs.
- -
-
Paragraph 0111
(2015/02/19)
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- Solid-phase synthesis of cyclic lipopeptidotriazoles
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The solid-phase synthesis of cyclic lipopeptidotriazoles derived from the cyclic decapeptide c(Lys-Lys2-Leu-Lys-Lys5-Phe-Lys-Lys- Leu-Gln) (BPC194), incorporating a triazolyl ring at Lys2 and a hexanoyl group at Lys5, was studied. Four different strategies that required the use of five orthogonal protecting groups (Fmoc, tBu, All, pNZ, ivDde) were explored. The influence of the side-chain protection of Lys 2 and Lys5 with the ivDde and pNZ groups was evaluated by incorporating Lys2(ivDde)/Lys5(pNZ) or Lys 2(pNZ)/Lys5(ivDde). The order of removal of these protecting groups and of the introduction of the hexanoyl and triazolyl moieties was also studied. The best strategy included: (i) synthesis of a cyclic peptidyl resin bearing Lys2(ivDde) and Lys5(pNZ); (ii) pNZ group removal; (iii) acylation with hexanoic acid; (iv) ivDde group removal; and (v) acylation with propiolic acid followed by an azide-alkyne 1,3-dipolar cycloaddition. By using this protocol, a set of cyclic lipopeptidotriazoles was prepared in high purities.
- Vila, Silvia,Camo, Cristina,Figueras, Eduard,Badosa, Esther,Montesinos, Emilio,Planas, Marta,Feliu, Lidia
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p. 4785 - 4794
(2014/08/05)
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- Design and synthesis of anti-cancer cyclopeptides containing triazole skeleton
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We describe the design and synthesis of some hypothetical heptapeptides specifically to overcome the neoplastic activity of ras oncogene and their anti-cancer activities were studied. To improve the anti-cancer activity of the synthesized peptides, their
- Tahoori, Fatemeh,Balalaie, Saeed,Sheikhnejad, Reza,Sadjadi, Mahnaz,Boloori, Parvin
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p. 1033 - 1046
(2014/05/06)
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- Chemical conjugation of an mRNA cap analogue with a cell-penetrating peptide as a potential membrane permeable translation inhibitor
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We present a versatile method for chemical conjugation of a dinucleotide cap analogue with a cell-penetrating peptide. The final coupling reaction is between an azide-modified peptide (MPS-N3)-a fragment that is responsible for transport of the conjugate through the cell membrane, with a biologically active compound-and an alkynylated cap structure, using the Cu(I)-catalyzed click reaction.
- Piecyk, Karolina,Jankowska-Anyszka, Marzena
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p. 606 - 609
(2014/01/23)
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- Synthesis and in vitro photodynamic activities of an integrin-targeting cRGD-conjugated zinc(II) phthalocyanine
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A 1,4-disubstituted zinc(II) phthalocyanine conjugated with a cyclic Arg-Gly-Asp-D-Phe-Lys (cRGDfK) moiety through a triazole linker was prepared and characterized by UV/Vis spectroscopy and high-resolution ESI-MS. The conjugate showed a relatively weak fluorescence emission in N,N-dimethylformamide (ΦF=0.08), but it was a very efficient singlet oxygen generator (ΦΔ=0.80) as a result of the di-α-substituted structure. Owing to the presence of the cyclic peptide sequence cRGDfK, which is a well-known αvβ3-integrin antagonist, this conjugate exhibited significantly higher cellular uptake toward the αvβ3+ U87-MG cells compared with the αvβ3- MCF-7 cells, as determined by flow cytometry and fluorescence microscopy. The photocytotoxicity of this compound against these two cell lines, however, was comparable owing to the similar efficiency of intracellular reactive oxygen species generation. Confocal microscopic studies also revealed that this conjugate localized preferentially in the lysosomes, but not in the nucleus, endoplasmic reticulum, and mitochondria of the U87-MG cells. Copyright
- Ke, Mei-Rong,Ng, Dennis K. P.,Lo, Pui-Chi
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p. 554 - 561
(2014/02/14)
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- Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides
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In this work, we report the synthesis of a thymine-functionalized nucleoamino acid suitable for the solid phase synthesis of nucleopeptides. The monomer was obtained in solution starting from commercial compounds and after NMR (1H and 13C) and ESIMS (positive ions) characterization it was used for the assembly of a cationic nucleopeptide obtained by sequentially introducing underivatized l-lysine units and nucleoamino acid monomers. After detachment from the resin, performed in acidic conditions, the oligomer was purified by HPLC and characterized by LC-ESIMS (positive ions) which confirmed the identity of the thymine-based nucleopeptide. The cationic nucleobase-containing peptide, well soluble in water, was studied by CD spectroscopy which allowed us to exclude any helical pre-organization of the nucleopeptide in the experimental conditions used. Furthermore, CD behavior of the oligomer at different temperatures was also studied as described in this work.
- Roviello, Giovanni N.,Musumeci, Domenica,D'Alessandro, Cristian,Pedone, Carlo
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p. 779 - 784
(2013/10/22)
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- Synthesis of cyclic peptidotriazoles with activity against phytopathogenic bacteria
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Cyclic peptidotriazoles derived from the antimicrobial cyclic peptide c(Lys-Lys-Leu-Lys-Lys-Phe-Lys-Lys-Leu-Gln) (BPC194) were prepared by incorporating a triazolyl amino acid at the 3-position. The synthesis was accomplished on solid-phase and involved a
- Gueell, Imma,Vila, Silvia,Micalo, Lluis,Badosa, Esther,Montesinos, Emilio,Planas, Marta,Feliu, Lidia
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p. 4933 - 4943
(2013/08/23)
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- REAGENTS AND METHODS FOR SIRTUIN CAPTURE
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The invention provides a method of preparing a sirtuin complex. The invention also provides a method of detecting a sirtuin in a sample comprising use of the aforesaid sirtuin complex.
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Page/Page column
(2013/03/28)
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- Method for preparing a reactive coating
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This invention is in the field of immuno chemistry and organic chemistry and provides means and methods for immobilizing a molecule, more in particular an antigen to a solid support. This allows for the economic and easy provision of immuno-assays, such as enzyme-linked immunosorbent assays. More in particular, the invention provides a method for immobilizing a bicycloalkyne to a solid support wherein a UV-reactive monomer is attached to the bicycloalkyne to obtain a UV-reactive clickable monomer, where after the UV-reactive clickable monomer is covalently linked to the solid support by means of UV irradiation in the presence of a photoinitiator.
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Page/Page column 5; 6
(2013/02/27)
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- Control of peptide assembly through directional interactions
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We demonstrate the self-assembly of tripeptide amphiphiles into spherical hollow capsules from linear nanoribbons via control of the molecular packing. We achieved a transition of arrangement from anisotropic to isotropic by an elaborate design of the molecular architecture.
- Choi, Inho,Park, Il-Soo,Ryu, Ja-Hyoung,Lee, Myongsoo
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experimental part
p. 8481 - 8483
(2012/09/21)
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- Real-time monitoring of cell apoptosis and drug screening using fluorescent light-up probe with aggregation-induced emission characteristics
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Real-time monitoring of cell apoptosis could provide valuable insights into early detection of therapy efficiency and evaluation of disease progression. In this work, we designed and synthesized a new live-cell-permeable, fluorescent light-up probe for real-time cell apoptosis imaging. The probe is comprised of a hydrophilic caspase-specific Asp-Glu-Val-Asp (DEVD) peptide and a hydrophobic tetraphenylethene (TPE) unit, a typical fluorogen with aggregation-induced emission characteristics. In aqueous solution, the probe is almost nonfluorescent but displays significant fluorescence enhancement in response to caspase-3/-7, which are activated in the apoptotic process and able to cleave the DEVD moieties. This fluorescence "turn-on" response is ascribed to aggregation of cleaved hydrophobic TPE residues, which restricts the intramolecular rotations of TPE phenyl rings and populates the radiative decay channels. The light-up nature of the probe allows real-time monitoring of caspase-3/-7 activities both in solutions and in living cells with a high signal-to-noise ratio. The probe provides a new opportunity to screen enzyme inhibitors and evaluate the apoptosis-associated drug efficacy.
- Shi, Haibin,Kwok, Ryan T. K.,Liu, Jianzhao,Xing, Bengang,Tang, Ben Zhong,Liu, Bin
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supporting information
p. 17972 - 17981
(2013/01/15)
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- New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: Dilute HCl in fluoro alcohol
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A novel method for cleaving from resin and removing acid-labile protecting groups for the Fmoc solid-phase peptide synthesis is described. 0.1 N HCl in hexafluoroisopropanol or trifluoroethanol cleanly and rapidly removes the tert-butyl ester and ether, Boc, trityl, and Pbf groups and cleaves the common resin linkers: Wang, HMPA, Rink amide, and PAL. Addition of just 5-10% of a hydrogen-bonding solvent considerably retards or even fully inhibits the reaction. However, a non-hydrogen-bonding solvent is tolerated.
- Palladino, Pasquale,Stetsenko, Dmitry A.
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supporting information
p. 6346 - 6349
(2013/02/25)
-
- Liquid-chromatography quantitative analysis of 20 amino acids after derivatization with FMOC-CI and its application to different origin Radix isatidis
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We developed a simple, rapid and reliable method for determination of 20 common amino acids based on derivatization with 9-fluorenylmethyl chloroformate (FMOC-CI) and RP-LC/UV, this method was first introduced into quantitative analysis of amino acids. The amino groups of amino acids were trapped with FMOC-CI to form amino acid-FMOC-Cl adducts which can be suitable for LC-UV. Chromatographic separation was performed on a C18 column with a mobile phase gradient consisting of acetonitrile and sodium acetate solution. This method was shown to be sensitive for 20 common amino acids. In the intra-day precisions assay, the range of RSDs was 3.21-7.67% with accuracies of 92.34-102.51%; for the inter-day precisions assay, the range of RSDs was 5.82-9.19% with accuracies of 90.25-100.63%. The results also indicated that solutions of amino acids-FMOC-Cl can be kept at room temperature for at least 24 h without showing significant losses in the quantified values. The validated method was successfully applied to the determination of major four kinds of amino acids in R. isatidis samples (Arg, Pro, Met and Val). The total content of amino acids in different origin R. isatidis was 13.32-19.16 mg/g. The differences between R. isatidis samples were large using HCA.
- Zhou, Wei,Zhang, Xiao-Yan,Duan, Geng-Li
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experimental part
p. 509 - 515
(2012/01/04)
-
- Synthesis of the Rheb and K-Ras4B GTPases
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Now available! Farnesylated and carboxymethylated Rheb (see picture) and K-Ras4B GTPases were synthesized in useful amounts by a combination of expressed protein ligation and solid-phase lipopeptide synthesis. The functionality of the proteins was proven by biochemical, biophysical, and cell-based investigations.
- Chen, Yong-Xiang,Koch, Sebastian,Uhlenbrock, Katharina,Weise, Katrin,Das, Debapratim,Gremer, Lothar,Brunsveld, Luc,Wittinghofer, Alfred,Winter, Roland,Triola, Gemma,Waldmann, Herbert
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supporting information; experimental part
p. 6090 - 6095
(2010/11/18)
-
- A universal and ready-to-use heterotrifunctional cross-linking reagent for facile synthetic access to sophisticated bioconjugates
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We describe for the first time, the synthesis and some bioconjugation applications of an original heterotrifunctional cross-linking reagent (also named tripod) bearing three different bioorthogonal functional groups which are fully compatible amongst themselves. Contrary to the first generation tripod recently reported by us (Org. Biomol. Chem., 2008, 6, 3065), the use of an azido group instead of the nucleophile-sensitive active carbamate moiety enables us to reach the targeted chemical orthogonality without the use of temporary aminooxy- and thiol protecting groups. Thus, the preparation of sophisticated bioconjugates through the sequential derivatisation of the tripod by means of copper-mediated 1,3-dipolar cycloaddition, oxime ligation and aqueous compatible mild thiol-alkylation reactions, is significantly simpler and more convenient. The chemoselective bioconjugation protocols were optimised through the preparation of FRET cassettes based on cyanine and/or xanthene fluorescent dye pairs and subsequent anchoring to fragile biomolecules. The applicability of this universal cross-linking reagent was also illustrated by the preparation of biochips suitable for aflatoxin B1 detection through the SPIT-FRI method.
- Clave, Guillaume,Volland, Herve,Flaender, Melanie,Gasparutto, Didier,Romieu, Anthony,Renard, Pierre-Yves
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body text
p. 4329 - 4345
(2010/11/18)
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- Supramolecular hydrogels for enzymatically triggered self-immolative drug delivery
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For the first time the combination of self-immolative spacers and supramolecular hydrogels has been tested in enzyme triggered drug release. Low-molecular weight drug-gelator conjugates have been prepared, which contain a gel forming lysine moiety linked to model drugs (benzylamine and phenethylamine) through a self-immolating spacer (p-aminobenzyloxycarbonyl). In the presence of trypsin the amide linkage between the gelator moiety and the spacer is hydrolyzed leading to the release of the model drug. This approach provides with distinct advantages, such as sustained release or versatility associated to the use of supramolecular hydrogels and self-immolative spacers, respectively.
- Sáez, José A.,Escuder, Beatriu,Miravet, Juan F.
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supporting information; experimental part
p. 2614 - 2618
(2010/05/17)
-
- Efficient procedure for the preparation of oligomer-free N-fmoc amino acids
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A two-step method is presented for the peptide-free, high-purity, and high-yield synthesis of N-Fmoc amino acids. The first step involves the preparation of stable dicyclohexylammonium-amino acid ionic adduct in acetone. Subsequently, the ionic adducts, on reaction with Fmoc-Nosu under mild alkaline conditions, give dipeptide-free N-Fmoc amino acids. The positive charge of the dicyclohexylammonium counterion in the ionic salt has a longer radius, moderating the nucleophilicity of the carboxylate ion of the amino acid and preventing by-products by arresting the formation of mixed anhydrides, the precursors of oligopeptide impurities.
- Nowshuddin, Shaik,Rao,Reddy, A. Ram
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experimental part
p. 2022 - 2031
(2009/11/30)
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- Activity-based high-throughput profiling of metalloprotease inhibitors using small molecule microarrays
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We herein describe a high-throughput small molecule microarray (SMM) method that enables quick and cost-effective identification of potent inhibitors of metalloproteases in an activity-dependent manner, thereby offering a rapid means for inhibitor discove
- Wang, Jun,Uttamchandani, Mahesh,Li, Ping Sun,Yao, Shao Q.
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p. 717 - 719
(2008/02/03)
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- Enzyme-cleavable linkers for peptide and glycopeptide synthesis
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Hydroxymethylphenoxy linkers that are commonly used in solid phase peptide synthesis are surprisingly susceptible to efficient cleavage by the protease chymotrypsin with a broad range of amino acid residues being tolerated at the scissile bond; this enzyme-cleavable linker system has been applied to peptide and glycopeptide synthesis. The Royal Society of Chemistry 2005.
- Maltman, Beatrice A.,Bejugam, Mallesham,Flitsch, Sabine L.
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p. 2505 - 2507
(2007/10/03)
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- Orthogonality and compatibility between Tsc and Fmoc amino-protecting groups
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New deprotection conditions that provide a complete orthogonality between Tsc and Fmoc amino-protecting groups are described. The potential of these orthogonal deprotection conditions was then demonstrated by the efficient solid-phase synthesis of branched peptides 20 and 21 using doubly protected amino acids such as Tsc-Lys(Fmoc)-OH 4c and Fmoc-Lys(Tsc)-OH 4d.
- Choi, Jin Seok,Kang, Hunhui,Jeong, Nakcheol,Han, Hogyu
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p. 2493 - 2503
(2007/10/03)
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- Developing photoactive affinity probes for proteomic profiling: Hydroxamate-based probes for metalloproteases
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The denaturing aspect of current activity-based protein profiling strategies limits the classes of chemical probes to those which irreversibly and covalently modify their targeting enzymes. Herein, we present a complimentary, affinity-based labeling appro
- Chan, Elaine W. S.,Chattopadhaya, Souvik,Panicker, Resmi C.,Huang, Xuan,Yao, Shao Q.
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p. 14435 - 14446
(2007/10/03)
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- Antiangiogenic peptides
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Mammalian kringle 5 fragments and kringle 5 fusion proteins are disclosed as a compounds for treating angiogenic diseases. Methods and compositions for inhibiting angiogenic diseases are also disclosed.
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- Towards a selective Boc deprotection on acid cleavable Wang resin
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Deprotection of the Boc group of an amino acid attached to the Wang resin has been investigated. Several conditions, including bases, solvents and reaction time, were studied. Quantitative yield of Boc deprotection was achieved with less than 10% loss of resin loading with trimethylsilyltriflate. This reagent allows the replacement of tert-butyl to TMS group, leading to a new temporary urethane protection readily hydrolyzed.
- Lejeune, Valérie,Martinez, Jean,Cavelier, Florine
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p. 4757 - 4759
(2007/10/03)
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- Amino acid derivatives as HIV aspartyl protease inhibitors
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The present invention relates to a class of amino acid derivatives with HIV aspartyl protease inhibitory properties.
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- Single-step formation of structurally defined bicyclic peptides via S(N)Ar cyclization.
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[structure: see text]. A solid-phase methodology for macrocyclization via an S(N)Ar reaction has been developed for the unambiguous formation of bicyclic peptidic compounds in a single cyclization step. The cyclization strategy involves the reaction of a
- Kohn,Zhang,Weigel
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p. 971 - 974
(2007/10/03)
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- Palmitoyl derivatives of GpMBP epitopes: T-cell response and peptidases susceptibility
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We report for the first time the immunoadjuvant effects of lipoconjugation of peptide antigens in an in vitro system by using CD4+ T-cells. The lipopeptides obtained by conjugating a palmitoyl moiety at the Nα-terminal of Gln74 or at
- Papini,Mazzanti,Nardi,Traggiai,Ballerini,Biagioli,Kalbacher,Beck,Deeg,Chelli,Ginanneschi,Massacesi,Vergelli
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p. 3504 - 3510
(2007/10/03)
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- A new practical strategy for the synthesis of long-chain phosphopeptide
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A new practical strategy has been developed for the synthesis of long-chain phosphopeptide. Both the 2-chlorobenzyloxycarbonyl (CIZ) group for Lys and methyl (Me) for phosphoamino acids remained intact, while other commonly used side-chain protecting groups were cleaved quantitatively, during the reaction using a highly acidic trifluoromethanesulfonic acid (TFMSA)-based reagent system (High TFMSA: TFMSA-TFA-m-cresol=1:9:1, v/v). Selective deprotection of the CIZ and Me group-containing protected phosphopeptide resin with the High TFMSA gave a partially protected phosphopeptide fragment suitable for thioester-mediated fragment condensation. A deprotection protocol of the 9-fluorenylmethyloxycarbonyl (Fmoc) group, which evades significant side reaction toward the protected phosphoamino acid, was also developed. These two new findings enabled us to synthesize long-chain phosphopeptide via thioester-mediated fragment condensation.
- Miyoshi,Otaka,Kaneko,Tamamura,Fujii
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p. 1230 - 1233
(2007/10/03)
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- The kinetic characterization of Escherichia coli MurG using synthetic substrate analogues
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Bacterial resistance to existing antibiotics poses a serious threat to human health. Because the peptidoglycan surrounding bacterial cells is essential for survival, the enzymes involved in peptidoglycan biosynthesis are attractive targets for the design
- Ha, Sha,Chang, Emmanuel,Lo, Mei-Chu,Men, Hongbin,Park, Peter,Ge, Min,Walker, Suzanne
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p. 8415 - 8426
(2007/10/03)
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- Extremely mild reagent for Boc deprotection applicable to the synthesis of peptides with thioamide linkages
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SnCl4 in organic solvents acts as an extremely mild reagent for Boc deprotection even in the presence of the acid-labile thioamide moiety with excellent yields.
- Frank, Robert,Schutkowski, Mike
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p. 2509 - 2510
(2007/10/03)
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