Chemo-enzymatic synthesis of tripeptide RGD diamide in organic solvents.
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%.
Huang
Yi-Bing
YB
Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130023, PR China.
Xiao
Yu-Peng
YP
Wang
Hua
H
Hou
Rui-Zhen
RZ
Zhang
Na
N
Wu
Xiao-Xia
XX
Xu
Li
L
Zhang
Xue-Zhong
XZ
D000577:Amides / Q000737:chemistry*; D004951:Esterification; D009842:Oligopeptides / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*
D000577:Amides; D009842:Oligopeptides; D009930:Organic Chemicals; D012997:Solvents; C047981:arginyl-glycyl-aspartic acid