title: One-pot synthesis of diverse DL-configuration dipeptides by a Streptomyces D-stereospecific amidohydrolase.
abstract: The synthesis of diverse DL-configuration dipeptides in a one-pot reaction was demonstrated by using a function of the aminolysis reaction of a D-stereospecific amidohydrolase from Streptomyces sp., a clan SE, S12 family peptidase categorized as a peptidase with D-stereospecificity. The enzyme was able to use various aminoacyl derivatives, including L-aminoacyl derivatives, as acyl donors and acceptors. Investigations of the specificity of the peptide synthetic activity revealed that the enzyme preferentially used D-aminoacyl derivatives as acyl donors. In contrast, L-amino acids and their derivatives were preferentially used as acyl acceptors. Consequently, the synthesized dipeptides had a DL-configuration when D- and L-aminoacyl derivatives were mixed in a one-pot reaction. This report also describes that the enzyme produced cyclo(D-Pro-L-Arg), a specific inhibitor of family 18 chitinase, with a conversion rate for D-Pro benzyl ester and L-Arg methyl ester to cyclo(D-Pro-L-Arg) of greater than 65%. Furthermore, based on results of cyclo(D-Pro-L-Arg) synthesis, we propose a reaction mechanism for cyclo(D-Pro-L-Arg) production.
authors.affiliation: Department of Agricultural, Biological, and Environmental Sciences, Faculty of Agriculture, Tottori University, Tottori 680-8553, Japan. arima@muses.tottori-u.ac.jp
authors.forename: Jiro
authors.initials: J
authors.lastname: Arima
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Usuki
authors.forename: Tadashi
authors.initials: T
authors.lastname: Hatanaka
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Mori
mesh_terms: D000581:Amidohydrolases / Q000378:metabolism*; D004151:Dipeptides / Q000737:chemistry* / Q000378:metabolism*; D013058:Mass Spectrometry; D008954:Models, Biological; D013237:Stereoisomerism; D013302:Streptomyces / Q000201:enzymology* / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D004151:Dipeptides; D000581:Amidohydrolases