- THE PREPARATION OF A PARTIALLY PROTECTED HEPTASACCHARIDE-ASPARAGINE INTERMEDIATE FOR GLYCOPEPTIDE SYNTHESIS
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The heptasaccharide O-α-D-mannopyranosyl-(1->6)-O-3)>-O-α-D-mannopyranosyl-(1->6)-O-3)>-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-glucopyranose, isol
- Nakabayashi, Satoru,Warren, Christopher D.,Jeanloz, Roger W.
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Read Online
- Mapping the landscape of potentially primordial informational oligomers: Oligodipeptides tagged with 2,4-disubstituted 5-aminopyrimidines as recognition elements
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(Chemical Equation Presented) Bit different: 2,4-Dioxo- and 2,4-diamino-5-aminopyrimidine nuclei attached to an oligodipeptide backbone display a disparity in their base-pairing strength which is opposite to that shown by corresponding triazines. This behavior points to a remarkable correlation between pairing strength and ΔpKa values of pairs of complementary bases.
- Mittapalli, Gopi Kumar,Osornio, Yazmin M.,Guerrero, Miguel A.,Reddy, Kondreddi Ravinder,Krishnamurthy, Ramanarayanan,Eschenmoser, Albert
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Read Online
- Total Synthesis of Malacidin A by β-Hydroxyaspartic Acid Ligation-Mediated Cyclization and Absolute Structure Establishment
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The development of novel antibiotics is critical to combating the growing emergence of drug-resistant pathogens. Malacidin A is a new member of the calcium-dependent antibiotic (CDAs) family with activity against antibiotic-resistant pathogens. Its mode of action is distinct from classical CDAs. However, the absolute structure of malacidin A has not been established. Herein, the total syntheses of malacidin A and its analogues are reported by a combination of Fmoc-based solid-phase peptide synthesis (SPPS) and β-hydroxyaspartic acid ligation-mediated peptide cyclization. The total synthesis enabled us to establish the absolute configuration of malacidin A, which is in agreement with those for natural malacidin A confirmed by advanced Marfey's analysis in our study.
- Brady, Sean F.,Chen, Sheng,Forelli, Nicholas,Li, Xuechen,Po, Kathy Hiu Laam,Shang, Zhuo,Sun, Zhenquan
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supporting information
p. 19868 - 19872
(2020/09/02)
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- Synthesis of constrained tetracyclic peptides by consecutive CEPS, CLIPS, and oxime ligation
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In Nature, multicyclic peptides constitute a versatile molecule class with various biological functions. For their pharmaceutical exploitation, chemical methodologies that enable selective consecutive macrocyclizations are required. We disclose a combination of enzymatic macrocyclization, CLIPS alkylation, and oxime ligation to prepare tetracyclic peptides. Five new small molecular scaffolds and differently sized model peptides featuring noncanonical amino acids were synthesized. Enzymatic macrocyclization, followed by one-pot scaffold-assisted cyclizations, yielded 21 tetracyclic peptides in a facile and robust manner.
- Streefkerk, Dieuwertje E.,Schmidt, Marcel,Ippel, Johannes H.,Hackeng, Tilman M.,Nuijens, Timo,Timmerman, Peter,Van Maarseveen, Jan H.
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supporting information
p. 2095 - 2100
(2019/04/11)
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- MULTICYCLIC PEPTIDES AND METHODS FOR THEIR PREPARATION
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The invention relates to methods for preparing a compound comprising a peptide attached to a molecular scaffold whereby multiple peptide loops are formed, to compounds that can be obtained with such methods and uses thereof.
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Page/Page column 50
(2018/06/30)
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- Synthesis and assay of retro-α4β1 integrin-targeting motifs
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In recent years, several research groups proposed new peptidomimetic antagonists of integrins αvβ3, α5β1, αIIbβ3, αvβ6, αvβ5, etc. based on retro sequences of the classic integrin-binding motif RGD. The retro strategy is still largely ignored for the non-
- Dattoli, Samantha D.,De Marco, Rossella,Baiula, Monica,Spampinato, Santi,Greco, Arianna,Tolomelli, Alessandra,Gentilucci, Luca
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supporting information
p. 225 - 232
(2014/01/23)
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- Parallel synthesis of an oligomeric imidazole-4, 5-dicarboxamide library
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A library of oligomeric compounds was synthesized based on the imidazole-4, 5-dicarboxylic acid scaffold along with amino acid esters and chiral diamines derived from amino acids. The final compounds incorporate nonpolar amino acids (Leu, Phe, Trp), polar amino acids (Ser, Asp, Arg), and neutral amino acids (Gly, Ala), and were designed to be useful in screening for inhibitors of protein-protein interactions. Many of the protected and deprotected oligomers show evidence of conformational isomers persistent at room temperature in aqueous solution. A total of 317 final oligomers, out of 441 targeted compounds, were obtained in high analytical purity and of sufficient quantity to submit them for high-throughput screening as part of the NIH Roadmap.
- Xu, Zhigang,DiCesare, John C.,Baures, Paul W.
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supporting information; experimental part
p. 248 - 254
(2010/08/19)
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- Synthesis of β-(S-methyl)thioaspartic acid and derivatives
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β-(S-Methyl)thioaspartic acid occurs as a posttranslational modification at position 88 in Escherichia coli ribosomal protein S12, a position that is a mutational hotspot resulting in both antibiotic-resistant and antibiotic-sensitive phenotypes. Critical
- Heredia-Moya, Jorge,Kirk, Kenneth L.
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p. 5908 - 5913
(2008/12/21)
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- Novel class of arylpiperazines containing N-acylated amino acids: Their synthesis, 5-HT1A, 5-HT2A receptor affinity, and in vivo pharmacological evaluation
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Novel arylpiperazines with N-acylated amino acids, selected on the basis of a preliminary screening of two libraries previously synthesized on SynPhase Lanterns, were prepared in solution and their affinity for 5-HT1A, 5-HT2A/s
- Zajdel, Pawel,Subra, Gilles,Bojarski, Andrzej J.,Duszynska, Beata,Tatarczynska, Ewa,Nikiforuk, Agnieszka,Chojnacka-Wojcik, Ewa,Pawlowski, Maciej,Martinez, Jean
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p. 2907 - 2919
(2008/02/01)
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- Novel C2-C3′ N-peptide linked macrocyclic taxoids. Part 2: Synthesis and biological activities of docetaxel analogues with a peptide side chain at C2 and their macrocyclic derivatives
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The synthesis of a series of novel docetaxel analogues possessing a peptide side chain at the C2 position as well as peptide macrocyclic taxoids is described. These compounds were designed to mimic a region of the α-tubulin loop equivalent to the paclitax
- Larroque, Anne-Laure,Dubois, Joelle,Thoret, Sylviane,Aubert, Genevieve,Chiaroni, Angele,Gueritte, Francoise,Guenard, Daniel
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p. 563 - 574
(2008/03/12)
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- Solution synthesis of a dimeric pentapeptide: Diketopiperazine cyclisation of Glu-Asp dipeptide esters and Asp-racemisation during segment condensation
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A haemoregulatory peptide analogue derived from the cystine-dimerised pentapeptide Glp-Glu-Asp-Cys-Lys-OH, in which the cystine residue has been replaced by an isosteric L,L-2,7-diaminosuberic acid moiety, was prepared by segment condensation in solution.
- Fischer,Solbakken,Undheim
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p. 2277 - 2288
(2007/10/02)
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