Chemo-enzymatic synthesis of tripeptide RGD diamide in organic solvents

J Biotechnol. 2005 Mar 2;116(1):51-9. doi: 10.1016/j.jbiotec.2004.10.004. Epub 2004 Dec 28.

Abstract

The tripeptide BzArgGlyAsp(NH(2))(2) was synthesized by a combination of chemical and enzymatic methods in this study. First of all, GlyAsp(NH(2))(2) was synthesized by a novel chemical method in three steps including chloroacetylation of L-aspartic acid, esterification of chloroacetyl L-aspartic acid and ammonolysis of chloroacetyl L-aspartic acid diethyl ester. Secondly, kinetically controlled synthesis of BzArgGlyAsp(NH(2))(2) catalyzed by trypsin in organic solvent was conducted. The optimum conditions are pH 8.0, 30 degrees C in ethanol/Tris-HCl buffer system (85:15, v/v) for 80 min in the maximum yield of 74.4%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Esterification
  • Oligopeptides / chemistry*
  • Organic Chemicals / chemistry*
  • Solvents / chemistry*

Substances

  • Amides
  • Oligopeptides
  • Organic Chemicals
  • Solvents
  • arginyl-glycyl-aspartic acid