title: Synthesis of a precursor dipeptide of RGDS (Arg-Gly-Asp-Ser) catalysed by the industrial protease alcalase.
abstract: 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%.
authors.affiliation: Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130021, People's Republic of China.
authors.forename: Rui-Zhen
authors.initials: RZ
authors.lastname: Hou
authors.forename: Yan
authors.initials: Y
authors.lastname: Yang
authors.forename: Gang
authors.initials: G
authors.lastname: Li
authors.forename: Yi-Bing
authors.initials: YB
authors.lastname: Huang
authors.forename: Hua
authors.initials: H
authors.lastname: Wang
authors.forename: Yun-Jia
authors.initials: YJ
authors.lastname: Liu
authors.forename: Li
authors.initials: L
authors.lastname: Xu
authors.forename: Xue-Zhong
authors.initials: XZ
authors.lastname: Zhang
mesh_terms: 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
chemical_list: D004151:Dipeptides; D009842:Oligopeptides; D009930:Organic Chemicals; D012997:Solvents; D014867:Water; C046617:arginyl-glycyl-aspartyl-serine; D013381:Subtilisins