- Synthesis of Prolylproline
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Prolylproline has been synthesized by both classical peptide synthesis method utilizing tert-butoxycarbonyl or trifluoroacetyl protection of the NH group and carbodiimide-promoted peptide bond formation and by opening of the dioxopiperazine ring in octahydrodipyrrolo[1,2-a:1′,2′-d]pyrazine-5,10-dione obtained by thermolysis of proline methyl ester.
- Gaidukevich,Popova,Zubreichuk,Knizhnikov
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- Permeation through phospholipid bilayers, skin-cell penetration, plasma stability, and CD spectra of α- And β-oligoproline derivatives
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After a survey of the special role, which the amino acid proline plays in the chemistry of life, the cell-penetrating properties of polycationic proline-containing peptides are discussed, and the widely unknown discovery by the Giralt group (J. Am. Chem. Soc. 2002, 124, 8876) is acknowledged, according to which fluorescein-labeled tetradecaproline is slowly taken up by rat kidney cells (NRK-49F). Here, we describe details of our previously mentioned (Chem. Biodiversity 2004, 1, 1111) observation that a hexa-β3-Pro derivative penetrates fibroblast cells, and we present the results of an extensive investigation of oligo-L- and oligo-D-α-prolines, as well as of oligo-β2h- and oligo-β3h-prolines without and with fluorescence labels (1-8; Fig. 1). Permeation through protein-free phospholipid bilayers is detected with the nanoFAST biochip technology (Figs. 2-4). This methodology is applied for the first time for quantitative determination of translocation rates of cell-penetrating peptides (CPPs) across lipid bilayers. Cell penetration is observed with mouse (3T3) and human foreskin fibroblasts (HFF; Figs. 5 and 6-8, resp.). The stabilities of oligoprolines in heparin-stabilized human plasma increase with decreasing chain lengths (Figs. 9-11). Time- and solvent-dependent CD spectra of most of the oligoprolines (Figs. 13 and 14) show changes that may be interpreted as arising from aggregation, and broadening of the NMR signals with time confirms this assumption. Copyright
- Kolesinska, Beata,Podwysocka, Dominika J.,Rueping, Magnus A.,Seebach, Dieter,Kamena, Faustin,Walde, Peter,Sauer, Markus,Windschiegl, Barbara,Meyer-ács, Mira,Vor Der Brüggen, Marc,Giehring, Sebastian
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- Synthesis of novel proline-based imidazolium ionic liquids
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Abstract: A series of eight novel proline functionalized dipeptide imidazolium ionic liquids (DPILs), i.e. Boc-[Pro-Pro-EMIM], Boc-[Pro-Val-EMIM], Boc-[Pro-Ala-EMIM], Boc-[Pro-Phe-EMIM] containing [Cl] and [NTf2] anions were synthesized via a f
- Chaubey, Snehkrishn A.,Patra, Niranjan,Mishra, Roli
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- Proline-Rich Short Peptides with Photocatalytic Activity for the Nucleophilic Addition of Methanol to Phenylethylenes
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Short proline-rich peptides were synthesized and modified with 1-(N,N-dimethylamino)pyrene by copper(I)-catalyzed cycloaddition. They perform photoredox catalysis of the nucleophilic addition of methanol to 1,1-diphenylethylene derivatives into products with Markovnikov orientation. The common additive triethylamine is avoided because forward and backward electron transfer is controlled by substrate binding. A free carboxylic function in the substrate allows more precise substrate binding and defines the electron transfer path better than the unspecific exciplex formation with the substrate bearing a carboxylic ester. A proline-type turn is an advantage for photoredox catalysis, but a proline-induced helix is not required. This is the first successful example for introducing secondarily structured peptides to photoredox catalysis.
- Hermann, Sergej,Sack, Daniel,Wagenknecht, Hans-Achim
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p. 2204 - 2207
(2018/06/04)
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- Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes
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Abstract: Stereoselective Michael addition of enolizable carbonyl compounds to a furane-derived nitroalkene was catalyzed by di- and tripeptide organocatalysts. The most competent catalysts were tripeptides possessing Pro–Pro–Glu structure. With aldehydes
- Polá?ková, Viera,?melová, Patrícia,Górová, Renáta,?ebesta, Radovan
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p. 729 - 736
(2017/12/26)
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- Factors Affecting the Stabilization of Polyproline II Helices in a Hydrophobic Environment
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Several parameters have a critical importance for the stabilization of either polyproline I (PPI) or polyproline II (PPII) helices in a hydrophobic environment. Among them, it was found out that the concentration is crucial as polyprolines at 3 mM concent
- Zanna, Nicola,Milli, Lorenzo,Del Secco, Benedetta,Tomasini, Claudia
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p. 1662 - 1665
(2016/04/26)
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- Compounds, compositions and use
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A peptide comprising a unit of formula (I) and having a molecular weight of less than 2000 wherein each X is independently an organic group, e.g. a C1-6 alkyl or C1-6 alkenyl group, preferably —CH2—CH═CH2, or th
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- Hybrid bombesin analogues: Combining an agonist and an antagonist in defined distances for optimized tumor targeting
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Radiolabeled hybrid ligands with defined distances between an agonist and an antagonist for the gastrin-releasing peptide receptor were found to have excellent tumor-targeting properties. Oligoprolines served as rigid scaffolds that allowed for tailoring distances of 10, 20, and 30 A between the recognition elements. In vitro and in vivo studies revealed that the hybrid ligand with a distance of 20 A between the recognition elements exhibits the highest yet observed tumor cell uptake and retention time in prostate cancer cells.
- Kroll, Carsten,Mansi, Rosalba,Braun, Friederike,Dobitz, Stefanie,Maecke, Helmut R.,Wennemers, Helma
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supporting information
p. 16793 - 16796
(2013/12/04)
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- Asymmetric catalysis at the mesoscale: Gold nanoclusters embedded in chiral self-assembled monolayer as heterogeneous catalyst for asymmetric reactions
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Research to develop highly versatile, chiral, heterogeneous catalysts for asymmetric organic transformations, without quenching the catalytic reactivity, has met with limited success. While chiral supramolecular structures, connected by weak bonds, are highly active for homogeneous asymmetric catalysis, their application in heterogeneous catalysis is rare. In this work, asymmetric catalyst was prepared by encapsulating metallic nanoclusters in chiral self-assembled monolayer (SAM), immobilized on mesoporous SiO2 support. Using olefin cyclopropanation as an example, it was demonstrated that by controlling the SAM properties, asymmetric reactions can be catalyzed by Au clusters embedded in chiral SAM. Up to 50% enantioselectivity with high diastereoselectivity were obtained while employing Au nanoclusters coated with SAM peptides as heterogeneous catalyst for the formation of cyclopropane- containing products. Spectroscopic measurements correlated the improved enantioselectivity with the formation of a hydrogen-bonding network in the chiral SAM. These results demonstrate the synergetic effect of the catalytically active metallic sites and the surrounding chiral SAM for the formation of a mesoscale enantioselective catalyst.
- Gross, Elad,Liu, Jack H.,Alayoglu, Selim,Marcus, Matthew A.,Fakra, Sirine C.,Toste, F. Dean,Somorjai, Gabor A.
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supporting information
p. 3881 - 3886
(2013/04/10)
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- PEG prodrug of gambogic acid: Amino acid and dipeptide spacer effects
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The clinical application of gambogic acid (GA), a natural component with promising antitumor activity, was limited due to its extremely poor aqueous solubility, rapid elimination in vivo, and wide biodistribution. To solve these problems, 30 poly(ethylene
- Ding, Ya,Zhang, Peng,Tang, Xiao-Yan,Zhang, Can,Ding, Song,Ye, Hai,Ding, Qi-Long,Shen, Wen-Bin,Ping, Qi-Neng
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experimental part
p. 1694 - 1702
(2012/08/08)
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- Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids
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A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated α-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4- dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-l-Orn(Boc)-Val-OMe, Fmoc-l-Cys(trt)-Gly-OEt and Boc-l-Tyr-Gly-OEt is presented.
- Nowshuddin, Shaik,Ram Reddy
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scheme or table
p. 22 - 25
(2011/04/18)
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- Reversing the enantioselectivity of a peptidic catalyst by changing the solvent
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The enantioselectivity of the peptidic catalyst H-Pro-Pro-Asp-NH(CH 2)11CH3 is reversed in different solvents. One enantiomer forms preferentially in pure DMSO or MeOH, whereas the other is preferentially formed in mixture
- Messerer, Matthias,Wennemers, Helma
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p. 499 - 502
(2011/04/22)
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- Design, synthesis and primary activity assay of bi- or tri-peptide analogues with the scaffold l-arginine as amino-peptidase N/CD13 inhibitors
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A series of bi- or tri-peptide analogues with the scaffold l-arginine were designed, synthesized and evaluated for their inhibitory activities against amino-peptidase N (APN) and metalloproteinase-2 (MMP-2). The primary activity assay showed that all the compounds exhibited higher inhibitory activities against APN than MMP-2. Within this series, compounds C6 and C7 (IC50 = 4.2 and 4.3 μM) showed comparable APN inhibitory activities with the positive control bestatin (IC50 = 3.8 μM).
- Mou, Jiajia,Fang, Hao,Liu, Yingzi,Shang, Luqing,Wang, Qiang,Zhang, Lei,Xu, Wenfang
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scheme or table
p. 887 - 895
(2010/05/02)
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- Synthesis of cyclic peptide analogues of the 310 helical Pro138-Gly144 segment of human aquaporin-4 by olefin metathesis
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Four cyclic pentapeptides and two cyclic heptapeptides modelled on the 310 helical Pro138-Gly144 segment of the water channel aquaporin-4 (AQP4) postulated to mediate adhesive interactions between AQP4 tetramers were synthesised by olefin metat
- Jacobsen, yvind,Klaveness, Jo,Petter Ottersen, Ole,Reza Amiry-Moghaddam, Mahmood,Rongved, Pal
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supporting information; experimental part
p. 1599 - 1611
(2009/06/28)
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- High stability of the polyproline II helix in polypeptide bottlebrushes
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Polymer bottlebrushes with monodisperse oligoproline side chains were efficiently synthesized, and the conformation of the peptide side chains in different solvents was investigated. Polymers with number-average degrees of polymerization (DPn)
- Zhang, Afang,Guo, Yifei
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experimental part
p. 8939 - 8946
(2009/09/25)
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- Manganese catalysed asymmetric cis-dihydroxylation with H2O 2
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High turnover enantioselective alkene cis-dihydroxylation is achieved with H2O2 catalysed by manganese based complexes containing chiral carboxylato ligands. The Royal Society of Chemistry.
- De Boer, Johannes W.,Browne, Wesley R.,Harutyunyan, Syuzanna R.,Bini, Laura,Tiemersma-Wegman, Theodora D.,Alsters, Paul L.,Hage, Ronald,Feringa, Ben L.
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supporting information; experimental part
p. 3747 - 3749
(2009/02/07)
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- Microwave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents
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A high-speed solution phase synthesis of peptide acids employing commercially available Fmoc-amino acid pentafluorophenyl esters as coupling agents has been demonstrated. The coupling has been found to be fast and completed in 30-45 sec. A simple work-up of the reaction mixture has resulted N-protected peptide acids in good yield. Utilizing the present method, the coupling of difficult sequences containing highly hindered α, α-dialkyl amino acids has also been demonstrated. Further, the synthesis of diastereomeric dipeptides, Fmoc-Phg-Phe-OMe and Fmoc-D-Phg-Phe-OMe revealed that the coupling is free from racemization.
- Suresh Babu, Vommina V.,Ramana Rao
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p. 2328 - 2332
(2007/10/03)
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- (Nitro) hymenamide A, unusual biologically active cyclic peptide
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A new biological active cyclic peptide (Nitro) Hymenamide A has been synthesized and the structure was established on the basis of analytical, IR, NMR and mass spectral data. The new compound was subjected to both antimicrobial and pharmacological studies.
- Belagali,Himaja,Kumar,Thomas,Prakasini,Poojary
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p. 160 - 164
(2007/10/03)
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- An Effective Water-Free Aprotic System for Dissolving Free Amino Acids
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An effective water-free system was proposed for dissolution and subsequent use in peptide synthesis of free amino acids and their derivatives. It consists of dimethylformamide, a tertiary base, and inorganic additives. Neutral salts (CF3COONa, Ba(ClO4)2, Ca(ClO4)2, NaClO4, BaI2, or Ca(NO3)2) serve as the inorganic additives that increase the solubility of free amino acids in dimethylformamide and provide true 0.2-3 M amino acid solutions. Triethylamine and N-methylmorpholine are most suitable as the tertiary bases. This system was used in reactions with acylating agents: Boc2O, ZOSu, FmocOSu, and activated derivatives of Nα-protected amino acids or peptides. The corresponding amino acid derivatives or Nα-protected di-, tri-, and tetrapeptides were obtained in yields of 80-99 percent at the reaction times of 30-240 min.
- Raydnov, M. G.,Klimenko, L. V.,Mitin, Yu. V.
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p. 283 - 287
(2007/10/03)
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- Synthetic and biological studies on 5-(p-chlorophenyl)furan-2-carboxyl peptides and 4-[2′-(5′-formyl)furyl]benzoyl peptides
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Substituted anilines are coupled with furoic acid and furfural at the position-5 to get 5-(p-chlorophenyl)furan-2-carboxylic acid and 4-[2′-(5′-formyl) furyl]benzoic acid which on further coupling with amino acid esters, di-, tetra- and hexapeptides yield
- Belagali,Harish Kumar,Boja, Poojary,Himaja
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p. 370 - 375
(2007/10/03)
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- STUDIES OF BITTER PEPTIDES FROM CASEIN HYDROLYZATE - VI. SYNTHESES AND BITTER TASTE OF BPIc (VAL-TYR-PRO-PHE-PRO-PRO-GLY-ILE-ASN-HIS) AND ITS ANALOGS AND FRAGMENTS.
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In order to investigate the relationship between chemical structure and bitter taste, the bitter peptide BPIc (Val-Tyr-Pro-Phe-Pro-Pro-Gly-Ile-Asn-His) isolated from casein hydrolyzate by Minamiura et al. and its analogs and fragments were synthesized. BPIc, whose threshold value of bitter taste was 0. 05 mm, was found to be one of the most bitter compounds, like quinine and phenylthiourea. However, left bracket Gly**5**,**6 right bracket - and left bracket Gly**9**,**1**0 right bracket -BPIc, and N-terminal octa- and heptapeptide fragments of BPIc possessed much weaker bitterness than BPIc. The results suggested that 5,6-proline and the basic nature of C-terminal are necessary for the strong bitterness exhibited by BPIc.
- Kanehisa
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- Studies of Bitter Peptides from Casein Hydrolyzate. I. Synthesis of Bitter Peptide BPIa Corresponding to Arg-Gly-Pro-Pro-Phe-Ile-Val from Casein Hydrolyzate by Alkaline Proteinase of Bacillus subtilis
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A bitter heptapeptide BPIa was synthesized and compared with the natural peptide, isolated by Minamiura et al. from casein hydrolyzate, by means of thin layer chromatography, paper electrophoresis, and carboxymethylcellulose column chromatography.All resu
- Fukui, Hiroshi,Kanehisa, Hidenori,Ishibashi, Norio,Miyake, Ichizo,Okai, Hideo
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p. 766 - 769
(2007/10/02)
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- Liquid-Phase Peptide Synthesis by Fragment Condensation on a Soluble Polymer Support. III. The Influence of the Content and the Chain Length of a Peptide Anchored to a Soluble Polymer Support on the Reactivity of the Amino-free Terminal of the Peptide
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In order to investigate the influence of the content and the chain length of a peptide anchored to a soluble polymer support on the reactivity of the amino-free terminal of the peptide, chloromethylated polystyrene, which is a starting material for peptid
- Narita, Mitsuaki,Itsuno, Shin-ichi,Hirata, Masanori,Kusano, Kazuya
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p. 1028 - 1033
(2007/10/02)
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