Synthesis of a precursor dipeptide of RGDS (Arg-Gly-Asp-Ser) catalysed by the industrial protease alcalase.
Synthesis of Bz-Arg-Gly-NH(2) (N-benzoylargininylglycinamide) [a precursor dipeptide of RGDS (Arg-Gly-Asp-Ser)] catalysed by protease in water/organic co-solvent systems was studied. Starting substrates were N-benzoyl-L-arginine ethyl ester hydrochloride (acyl donor) and glycinamide (nucleophile). Acetonitrile was selected as the organic solvent. Alcalase, an industrial alkaline protease, was applied to the synthesis of the target dipeptide. The conditions of the synthesis reaction were optimized by examining the effects of several factors, including water content, temperature, pH, molar ratio of the substrates and reaction time, on the yield of Bz-Arg-Gly-NH(2). The optimum conditions were established to be pH 10.0, 45 degrees C, in acetonitrile/0.1 M Na(2)CO(3)/NaHCO(3) buffer system (90:10, v/v) for 1 h with a dipeptide yield of 82.9%.
Hou
Rui-Zhen
RZ
Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130021, People's Republic of China.
Yang
Yan
Y
Li
Gang
G
Huang
Yi-Bing
YB
Wang
Hua
H
Liu
Yun-Jia
YJ
Xu
Li
L
Zhang
Xue-Zhong
XZ
D002384:Catalysis; D004151:Dipeptides / Q000138:chemical synthesis*; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009842:Oligopeptides / Q000138:chemical synthesis*; D009930:Organic Chemicals / Q000737:chemistry*; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D013381:Subtilisins / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D004151:Dipeptides; D009842:Oligopeptides; D009930:Organic Chemicals; D012997:Solvents; D014867:Water; C046617:arginyl-glycyl-aspartyl-serine; D013381:Subtilisins