Alcalase-catalyzed, kinetically controlled synthesis of a precursor dipeptide of RGDS in organic solvents.
The protease-catalyzed, kinetically controlled synthesis of a precursor dipeptide of RGDS, Z-Asp-Ser-NH2 in organic solvents was studied. Alcalase, an industrial alkaline protease, was used to catalyze the synthesis of the target dipeptide in water-organic cosolvents systems with Z-Asp-OMe as the acyl donor and Ser-NH2 as the nucleophile. Acetonitrile was selected as the organic solvent from acetonitrile, ethanol, methanol, DMF, DMSO, ethyl acetate, 2-methyl-2-propanol, and chloroform tested under the experimental conditions. The conditions of the synthesis reaction were optimized by examining the effects of several factors, including water content, temperature, pH, and reaction time on the Z-Asp-Ser-NH2 yields. The optimum conditions are pH 10.0, 35 degrees C, in acetonitrile/Na2CO3-NaHCO3 buffer system (85:15, v/v), 6 h, with a dipeptide yield of 75.5%.
Hou
Rui-Zhen
RZ
Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun, P. R. China.
Yang
Yan
Y
Huang
Yi-Bing
YB
Wang
Hua
H
Zhang
Na
N
Liu
Yun-Jia
YJ
Zhang
Xue-Zhong
XZ
Li
Gang
G
D000097:Acetonitriles / Q000737:chemistry; D001224:Aspartic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000378:metabolism; D001407:Bacillus / Q000201:enzymology; D002384:Catalysis; D002850:Chromatography, Gel; D003911:Dextrans / Q000737:chemistry; D004151:Dipeptides / Q000096:biosynthesis* / Q000302:isolation & purification; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009842:Oligopeptides / Q000096:biosynthesis*; D009930:Organic Chemicals / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000378:metabolism; D012997:Solvents / Q000737:chemistry*; D013381:Subtilisins / Q000737:chemistry / Q000378:metabolism*; D013696:Temperature; D014867:Water / Q000737:chemistry
D000097:Acetonitriles; D003911:Dextrans; D004151:Dipeptides; D009842:Oligopeptides; D009930:Organic Chemicals; D012997:Solvents; D014867:Water; D001224:Aspartic Acid; D012694:Serine; C025614:sephadex; C046617:arginyl-glycyl-aspartyl-serine; D013381:Subtilisins; C032159:acetonitrile