- 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; 51
(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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- Non-proteinogenic amino acids in the pThr-2 position of a pentamer peptide that confer high binding affinity for the polo box domain (PBD) of polo-like kinase 1 (Plk1)
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We report herein that incorporating long-chain alkylphenyl-containing non-proteinogenic amino acids in place of His at the pT-2 position of the parent polo-like kinase 1 (Plk1) polo box domain (PBD)-binding pentapeptide, PLHSpT (1a) increases affinity. Fo
- Qian, Wen-Jian,Park, Jung-Eun,Lee, Kyung S.,Burke Jr., Terrence R.
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supporting information
p. 7306 - 7308
(2013/02/22)
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- Determination of long-range distances and dynamic order parameters by dipolar recoupling in high-resolution magic-angle spinning NMR spectroscopy
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By introducing dipolar recoupling methods to high-resolution magic-angle spinning (HRMAS) NMR spectroscopy, a class of experiments has been delevoped that allows the measurement of residual dipole-dipole couplings of ～1 Hz in weakly immobilized molecules.
- Thieme, Karena,Schnell, Ingo
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p. 12100 - 12101
(2007/10/03)
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- Ready protease-catalyzed synthesis of carbohydrate-amino acid conjugates.
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The protease-catalyzed synthesis of amino acid est-carbohydrate conjugates as glycopeptide analogues has been achieved in a highly regioselective and carbohydrate-specific manner using amino acid vinyl ester acyl donors and minimally or completely unprotected carbohydrate acyl acceptors, which together probed active sites of proteases to reveal yield efficiencies that are modulated by the carbohydrate C-2 substitutent, and that may be exploited to allow selective one-pot syntheses.
- Boyer,Stanchev,Fairbanks,Davis
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p. 1908 - 1909
(2007/10/03)
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- 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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p. 279 - 290
(2007/10/02)
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