Suppression of epimerization by cupric (II) salts in peptide synthesis using free amino acids as amino components

差向异构体 碳二亚胺 化学 氨基酸 试剂 有机化学 药物化学 立体化学 生物化学
作者
Maxim G. Ryadnov,LYCBOV V. KLIMENKO,Yuri V. Mitin
出处
期刊:Journal of Peptide Research [Wiley]
卷期号:53 (3): 322-328 被引量:14
标识
DOI:10.1034/j.1399-3011.1999.00034.x
摘要

An epimerization‐free system for coupling N‐protected peptides with free amino acids was developed. A number of inorganic substances were tested as epimerization suppressant additives during the coupling by various methods (carbodiimide plus additives, uronium salts, Woodward’s reagent‐K, isobutyl‐chloroformate, etc.). Some of them (ZnCl 2 , RbClO 4 , LiCl, SnCl 4 , AlCl 3 , etc.) in combination with some coupling methods can guarantee coupling with minimal epimerization ( D ‐epimer < 1%). But only a simultaneous use of 1‐hydroxybenzotriazole and Cu 2+ ions as additives in carbodiimide‐mediated peptide couplings appeared to give a standard result ( D ‐epimer < 0.1%). There was no epimerization even in the case when N‐methyl amino acid (sarcosine) was used as an amino component, while in the absence of Cu 2+ ions an unacceptable level of epimerization was observed ( D ‐epimer, 22% for carbodiimide with the 1‐hydroxybenzotriazole method). So far it has been considered that Cu 2+ ions prevent obtaining peptides in high yields (< 90%) by various coupling methods. We have found that the use of 1‐hydroxybenzotriazole, CuCl 2 and 1‐ethyl‐3‐(3‐dimethylaminopropyl) carbodiimide instead of dicyclohexylcarbodiimide provides a possible method for obtaining the desired peptides in 90–99% yields without epimerization. All these results were shown by employing several model peptide couplings with free amino acids as amino components dissolved in an effective solvent system which readily dissolved them.
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