- SUPRAMOLECULAR GEL SUPPORTED ON OPEN-CELL POLYMER FOAM
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The present invention relates to a polymer foam, said polymer foam comprising pores forming an open-cell polymer foam, said polymer foam comprising a supramolecular gel inside pores, and said polymer foam comprising at least one enzyme. The present invention relates to a supramolecular gel; its preparation and its applications, notably in chemical synthesis and kinetic resolution, in particular of organic compounds. The present invention also relates to flow chemistry.
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Page/Page column 16-17; 21
(2021/03/19)
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- A Neutrophil-Inspired Supramolecular Nanogel for Magnetocaloric–Enzymatic Tandem Therapy
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Neutrophils can responsively release reactive oxygen species (ROS) to actively combat infections by exogenous stimulus and cascade enzyme catalyzed bio-oxidation. A supramolecular nanogel is now used as an artificial neutrophil by enzymatic interfacial se
- Chen, Mengwei,Cheng, Yu,Lesniak, Maciej S.,Mi, Yongli,Wang, Jingjing,Wang, Qigang,Wang, Xia,Wu, Chu,Wu, Jiaojiao,Wu, Qing,Zhang, Qi
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p. 3732 - 3738
(2020/02/04)
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- Enzyme Instructed Self-assembly of Naphthalimide-dipeptide: Spontaneous Transformation from Nanosphere to Nanotubular Structures that Induces Hydrogelation
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Understanding the structure-morphology relationships of self-assembled nanostructures is crucial for developing materials with the desired chemical and biological functions. Here, phosphate-based naphthalimide (NI) derivatives have been developed for the
- Chakravarthy, Rajan Deepan,Lin, Hsin-Chieh,Mohammed, Mohiuddin
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supporting information
(2020/08/03)
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- Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety
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Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.
- Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong
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p. 1080 - 1090
(2020/05/25)
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- Synthesis and anticancer activities of proline-containing cyclic peptides and their linear analogs and congeners
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A solution phase method was adopted for the synthesis of proline-containing cyclic pentapeptide 2 and total synthesis of naturally occurring cyclic heptapeptide Reniochalistatin B 3. For the synthesis of 3, both divergent and convergent strategies were used to improve the overall yield from 12 to 25%. Different N and C terminal modified linear analogs and congeners of 2 and 3 were synthesized. Both cyclic peptides 2 and 3 and their linear analogs/congeners were evaluated for anti-cancer activity against HeLa cell line, among which pentapeptide 2 h and hexapeptide 3n with N-terminal protected hexafluoroisopropyl carbamates (HFIPC) interestingly showed higher cytotoxicity with an IC50 of 2.73 and 4.3 μM, respectively compared to their Boc-protected analogs 2a (IC50 20 μM) and 3c (IC50 38.51 μM) and cyclic peptides 2 (>100 μM) and 3 (47 μM). These results were further validated by biological experiments such as colony formation and wound healing assays.
- Ghosh, Keshab Ch,Duttagupta, Indranil,Bose, Chandra,Banerjee, Priyanjalee,Gayen, Anuran Kumar,Sinha, Surajit
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supporting information
p. 221 - 236
(2019/01/19)
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- Supramolecular Platform Stabilizing Growth Factors
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High concentrations of supplemented growth factors can cause oversaturation and adverse effects in in vitro and in vivo studies, though these supraphysiological concentrations are often required due to the low stability of growth factors. Here we demonstrate the stabilization of TGF-β1 and BMP4 using supramolecular polymers. Inspired by heparan sulfate, sulfonated peptides were presented on a supramolecular polymer to allow for noncovalent binding to growth factors in solution. After mixing with excipient molecules, both TGF-β1 and BMP4 were shown to have a prolonged half-life compared to the growth factors free in solution. Moreover, high cellular response was measured by a luciferase assay, indicating that TGF-β1 remained highly active upon binding to the supramolecular assembly. The results demonstrate that significant lower concentrations of growth factors can be used when supramolecular polymers bearing growth factor binding moieties are implemented. This approach can also be exploited in hydrogel systems to control growth factor release.
- Hendrikse, Simone I. S.,Spaans, Sergio,Meijer,Dankers, Patricia Y. W.
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p. 2610 - 2617
(2018/05/14)
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- Photoinduced electron transfer-promoted debenzylation of phenylalanine and tyrosine derivatives using dicyanoarene
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Photoinduced debenzylations of phenylalanine and tyrosine derivatives with dicyanoarenes afford glycine derivatives by the generation of radical cations. Despite the limited substrate scope, the radical cation of phenylalanine and tyrosine derivatives bearing both a carbamate (without an aromatic group) at the N-terminal and an amide at the C-terminal could promote the breaking C–C bond at the benzylic position by a photoinduced electron transfer. It is important to understand the chemical behavior of the radical cations of phenylalanine and tyrosine in enzymes involving electron transfer.
- Yamawaki, Mugen,Okita, Yoshiki,Yamamoto, Takashi,Morita, Toshio,Yoshimi, Yasuharu
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p. 7239 - 7244
(2017/11/20)
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- Toward the Rational Design of Galactosylated Glycoclusters That Target Pseudomonas aeruginosa Lectin A (LecA): Influence of Linker Arms That Lead to Low-Nanomolar Multivalent Ligands
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Anti-infectious strategies against pathogen infections can be achieved through antiadhesive strategies by using multivalent ligands of bacterial virulence factors. LecA and LecB are lectins of Pseudomonas aeruginosa implicated in biofilm formation. A series of 27 LecA-targeting glycoclusters have been synthesized. Nine aromatic galactose aglycons were investigated with three different linker arms that connect the central mannopyranoside core. A low-nanomolar (Kd=19 nm, microarray) ligand with a tyrosine-based linker arm could be identified in a structure–activity relationship study. Molecular modeling of the glycoclusters bound to the lectin tetramer was also used to rationalize the binding properties observed.
- Wang, Shuai,Dupin, Lucie,No?l, Mathieu,Carroux, Cindy J.,Renaud, Louis,Géhin, Thomas,Meyer, Albert,Souteyrand, Eliane,Vasseur, Jean-Jacques,Vergoten, Gérard,Chevolot, Yann,Morvan, Fran?ois,Vidal, Sébastien
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supporting information
p. 11785 - 11794
(2016/08/05)
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- Glutamic Acid Selective Chemical Cleavage of Peptide Bonds
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Site-specific hydrolysis of peptide bonds at glutamic acid under neutral aqueous conditions is reported. The method relies on the activation of the backbone amide chain at glutamic acid by the formation of a pyroglutamyl (pGlu) imide moiety. This activation increases the susceptibility of a peptide bond toward hydrolysis. The method is highly specific and demonstrates broad substrate scope including cleavage of various bioactive peptides with unnatural amino acid residues, which are unsuitable substrates for enzymatic hydrolysis.
- Nalbone, Joseph M.,Lahankar, Neelam,Buissereth, Lyssa,Raj, Monika
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supporting information
p. 1186 - 1189
(2016/03/15)
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- Design and construction of higher-order structure and function in proteinosome-based protocells
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The design and construction of higher-order structure and function in proteinosome microcompartments enclosed by a cross-linked membrane of amphiphilic bovine serum albumin/poly(N-isopropylacrylamide) (BSA-NH 2/PNIPAAm) nanoconjugates is descri
- Huang, Xin,Patil, Avinash J.,Li, Mei,Mann, Stephen
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supporting information
p. 9225 - 9234
(2014/07/08)
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- Mechanistic insights into phosphatase triggered self-assembly including enhancement of biocatalytic conversion rate
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We report on the mechanistic investigation of alkaline phosphatase (AP) triggered self-assembly and hydrogelation of Fmoc-tyrosine (Fmoc-Y). We studied separately the biocatalytic conversion using HPLC, changes in supramolecular interactions and chirality
- Thornton, Kate,Abul-Haija, Yousef M.,Hodson, Nigel,Ulijn, Rein V.
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p. 9430 - 9439
(2013/10/01)
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- Cerium oxide nanoparticle-mediated self-assembly of hybrid supramolecular hydrogels
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Hybrid supramolecular hydrogels are prepared by non-enzymatic dephosphorylation of N-fluorenylmethyloxycarbonyl tyrosine-(O)-phosphate (FMOC-Tyr-P) using catalytic cerium oxide nanoparticles. The organic-inorganic hydrogels exhibit enhanced viscoelastic p
- Patil, Avinash J.,Kumar, Ravinash Krishna,Barron, Nicholas J.,Mann, Stephen
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supporting information; scheme or table
p. 7934 - 7936
(2012/09/22)
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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)
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- Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids
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Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20° as reagents to introduce -amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC. Georg Thieme Verlag Stuttgart - New York.
- Ibrahim, Tarek S.,Tala, Srinivasa R.,El-Feky, Said A.,Abdel-Samii, Zakaria K.,Katritzky, Alan R.
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p. 2013 - 2016
(2011/10/08)
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- 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)
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- Synthesis and characterization of a novel ester-based nucleoamino acid for the assembly of aromatic nucleopeptides for biomedical applications
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In this work, we report a technological approach to a novel Fmoc-protected nucleoamino acid, based on l-tyrosine, carrying the DNA nucleobase on the hydroxyl group by means of an ester bond, suitable for the solid-phase synthesis of novel aromatic nucleopeptides of potential interest in biomedicine. After ESI-MS and NMR characterization this building block was used for the assembly of a thymine-functionalized tetrapeptide, composed of nucleobase-containing and underivatized l-tyrosine moieties alternated in the backbone.
- Roviello, Giovanni N.,Musumeci, Domenica,Bucci, Enrico M.,Pedone, Carlo
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experimental part
p. 206 - 210
(2012/06/04)
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- MULTIFUNCTIONAL SUPRAMOLECULAR HYDROGELS AS BIOMATERIALS
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The present invention pertains to the design and application of a supramolecular hydrogel having a three-dimensional, self-assembling, elastic, network structure comprising non-polymeric, functional molecules and a liquid medium, whereby the functional mo
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Page/Page column title page; 5; 13; 14; 24; sheet 5
(2008/06/13)
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- Photogenerated reagents
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This invention describes reagent precursors and methods for chemical and biochemical reactions. These reagent precursors that can be activated in solution upon irradiation to generate reagents required for the subsequent chemical reactions. Specifically, photogenerated reagents (PGR) are useful for controlling parallel combinatorial synthesis and various chemical and biochemical reactions.
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Page/Page column 20-21
(2008/06/13)
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- Alternative and chemoselective deprotection of the α-amino and carboxy functions of N-Fmoc-amino acid and N-Fmoc-dipeptide methyl esters by modulation of the molar ratio in the AlCl3/N,N-dimethylaniline reagent system
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The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N- dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Di Gioia, Maria Luisa,Leggio, Antonella,Le Pera, Adolfo,Liguori, Angelo,Perri, Francesca,Siciliano, Carlo
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p. 4437 - 4441
(2007/10/03)
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- TMS Triflate-Catalyzed Cleavage of Prenyl (3-Methylbut-2-enyl) Ester
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(Matrix Presented) Prenyl (3-methylbut-2-enyl) ester is catalytically cleaved by TMS triflate affording carboxylic acid and isoprene in high yield under mild conditions with high chemoselectivity without causing epimerization of the neighboring chiral cen
- Nishizawa, Mugio,Yamamoto, Hirofumi,Seo, Ken,Imagawa, Hiroshi,Sugihara, Takumichi
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p. 1947 - 1949
(2007/10/03)
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- Facile solid-phase synthesis of sulfated tyrosine-containing peptides: Total synthesis of human big gastrin-II and cholecystokinin (CCK)-39
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Chemical synthesis of tyrosine O-sulfated peptides is still a laborious task for peptide chemists because of the intrinsic acid-lability of the sulfate moiety. An efficient cleavage/deprotection procedure without loss of the sulfate is the critical difficulty remaining to be solved for fluoren-9-ylmethoxycarbonyl (Fmoc)-based solid-phase synthesis of sulfated peptides. To overcome the difficulty, TFA-mediated solvolysis rates of a tyrosine O-sulfate [Tyr(SO3H)] residue and two protecting groups, tBu for the hydroxyl group of Ser and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf) for the guanidino group of Arg, were examined in detail. The desulfation obeyed first-order kinetics with a large entropy (59.6 J·K-1·mol-1) and enthalpy (110.5 kJ·mol-1) of activation. These values substantiated that the desulfation rate of the rigidly solvated Tyr(SO3H) residue was strongly temperature-dependent. By contrast, the SN1-type deprotections were less temperature-dependent and proceeded smoothly in TFA of a high ionizing power. Based on the large rate difference between the desulfation and the SN1-type deprotections in cold TFA, an efficient deprotection protocol for the sulfated peptides was developed. Our synthetic strategy for Tyr(SO3H)containing peptides with this effective deprotection protocol is as follows: (i) a sulfated peptide chain is directly constructed on 2-chlorotrityl resin with Fmoc-based solid-phase chemistry using Fmoc-Tyr(SO3Na)-OH as a building block; (ii) the protected peptide-resin is treated with 90% aqueous TFA at 0 °C for an appropriate period of time for the cleavage and deprotection. Human cholecystokinin (CCK)-12, mini gastrin-II (14 residues), and little gastrin-II (17 residues) were synthesized with this method in 26-38% yields without any difficulties. This method was further applied to the stepwise synthesis of human big gastrin-II (34 residues), CCK-33 and -39. Despite the prolonged acid treatment (15-18 h at 0 °C), the ratios of the desulfated peptides were less than 15%, and the pure sulfated peptides were obtained in around 10% yields.
- Kitagawa,Aida,Fujiwara,Yagami,Futaki,Kogire,Ida,Inoue
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- Apparatus and methods for detecting antibodies
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A single, unitary, solid phase support apparatus having a planar surface divided into a plurality of separate zone functions to detect antibodies. Each zone has bonded to it, a different peptide through its C-terminal end. The zones are incubated with the analyte sample and observed for reaction, indicating the virus-specific or bacteria specific presence or absence.
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- Kinetic analysis of a protein tyrosine kinase reaction transition state in the forward and reverse directions
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Protein tyrosine kinases catalyze the transfer of the γ-phosphoryl group from ATP to tyrosine residues in proteins and are important enzymes in cell signal transduction. We have investigated the catalytic phosphoryl transfer transition state of a protein tyrosine kinase reaction catalyzed by Csk by analyzing a series of fluorotyrosine-containing peptide substrates. It was established for five such fluorotyrosine-containing peptide substrates that there is good agreement between the tyrosine analogue phenol pK(a) and the ionizable group responsible for the basic limb of a pH rate profile analysis. This indicates that the substrate tyrosine phenol must be neutral to be enzymatically active. Taken together with previous data indicating a small β(nucleophile) coefficient (0-0.1), these results strongly support a dissociative transition state for phosphoryl transfer. In addition, the β(leaving group) coefficient was measured for the reverse protein tyrosine kinase reaction and shown to be -0.3. This value is in good agreement with a previously reported nonenzymatic model phosphoryl transfer reaction carried out under acidic conditions (pH 4) and is most readily explained by a transition state with significant proton transfer to the departing phenol.
- Kim, Kyonghee,Cole, Philip A.
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p. 6851 - 6858
(2007/10/03)
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- Potential formation of intramolecular inclusion complexes in peptidocyclodextrins as evidenced by NMR spectroscopy
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Investigations of the structure of β- and γ-cyclodextrin derivatives in solution obtained by grafting amino acids or peptides are presented.These compounds are models for vectorization-dedicated molecular carriers.It is shown that for some amino acids, strong intramolecular self-inclusion complexes are formed in aqueous solution.This process strongly depends upon the nature and position of the pertinent amino acid in the peptide sequence.Two dimensional NMR experiments are used in conjunction with competition with external guests to evidence and estimate the strength of these auto-inclusion complexes.
- Djedaini-Pilard, Florence,Azaroual-Bellanger, Nathalie,Gosnat, Muriel,Vernet, Delphine,Perly, Bruno
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p. 723 - 730
(2007/10/02)
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- Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis
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Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis.The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined.On the basis of these data, the bis-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO3MDPSE2)-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides.The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.
- Chao, Hann-Guang,Bernatowicz, Michael S.,Reiss, Paul D.,Matsueda, Gary R.
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p. 6687 - 6691
(2007/10/02)
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- Evaluation of the final deprotection system for the solid-phase synthesis of tyr(SO3H)-containing peptides with 9-fluorenylmethyloxycarbonyl (Fmoc)-strategy and its application to the synthesis of cholecystokinin (CCK)-12
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Acidolytic deprotection and cleavage conditions for an acid-labile Tyr(SO3H)-containing peptide were systematically examined with respect to acid, temperature, and scavenger. The 90% aqueous trifluoroacetic acid (TFA)-based reagent systems (90%
- Yagami,Shiwa,Futaki,Kitagawa
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p. 376 - 380
(2007/10/02)
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- Glycosylation of Phenols: Preparation of 1,2-cis and 1,2-trans Glycosylated Tyrosine Derivatives to be used in Solid-phase Glycopeptide Synthesis
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The synthesis of four building blocks, Nα-Fmoc-Tyr(Ac4-β-D-Glc)-OPfp 6, Nα-Fmoc-Tyr(Bz4-α-D-Glc)-OPfp 16, Nα-Fmoc-Tyr4-α-D-Glc-(1->4)-Ac3-β-D-Glc>-OPfp 9 and Nα-Fmo
- Jensen, Knud J.,Meldal, Morten,Bock, Klaus
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p. 2119 - 2130
(2007/10/02)
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- Peptides with sulfate ester groups
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Novel peptides having sulfate ester groups and containing 6 to 9 amino acids; possessing feeding inhibition properties and capable of stimulating the contraction of the gallbladder. Also methods of treating and preventing obesity in which these novel peptides or other specified peptides can be used.
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- Method for the production of amino terminus protected naturally occurring amino acids
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A method for the production of substantially 100% pure Nα-urethane protected amino acids is disclosed. This method eliminates the formation of di-peptide and tri-peptide contaminants. Reaction of blocking reagents at the carboxylate site on a protected peptide is prevented by the application of labile amino acid esters. Subsequent removal of the ester yields, in ultra-high purity, the Nα-protected amino acid. The substantially 100% pure Nα-urethane protected amino acid are also disclosed.
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- Fmoc-polyamide solid phase synthesis of an O-phosphotyrosine-containing tridecapeptide
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The incorporation of O-phosphotyrosine into synthetic peptides using Fmoc-Tyr(PO3Me2)-OH in the Fmoc-polyamide procedure is described with the preparation of the model PTyr-tridecapeptide sequence H-Arg-Leu-Ile-Glu-Asp-Asn-Glu-PTyr-T
- Kitas,Perich,Wade,Johns,Tregear
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p. 6229 - 6232
(2007/10/02)
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- Process for the solid phase synthesis of peptides which contain sulfated tyrosine
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Peptides and Peptide amides such as cholecystokinin (CCK-8) are synthesized in improved yields and purity by a solid phase process. The requisite protected peptide is elaborated and sulfated on a solid support, deprotected, and cleaved from the solid support to give the total synthesis of CCK-8 on a solid support. Thereafter, the peptide is purified in a single step by ion exchange chromatography to provide analytically pure CCK-8.
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- 9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters
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9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.
- Schoen, Istvan,Kisfaludy, Lajos
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p. 303 - 305
(2007/10/02)
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