title: Development of an efficient enzymatic production of gamma-D-glutamyl-L-tryptophan (SCV-07), a prospective medicine for tuberculosis, with bacterial gamma-glutamyltranspeptidase.
abstract: Gamma-D-Glutamyl-L-tryptophan (SCV-07) is a prospective medicine for the treatment of tuberculosis, according to the phase two clinical trial. Because gamma-D-glutamyl-L-tryptophan has several reactive groups in its molecule, consists of D- and L-amino acids, and is connected by gamma-glutamyl linkage, its chemical synthesis is complicated. An efficient enzymatic method to synthesize gamma-D-glutamyl-L-tryptophan from D-glutamine and L-tryptophan employing bacterial gamma-glutamyltranspeptidase was developed. The optimum reaction conditions were 50 mM D-glutamine, 50 mM L-tryptophan, and 0.2 U ml(-1) gamma-glutamyltranspeptidase, pH 9-9.5, and incubation at 37 degrees C for 5 h. After a 5 h incubation, 33 mM gamma-D-glutamyl-L-tryptophan was obtained, the conversion rate being 66%. The product was purified by Dowex 1 x 8 column and was considered to be gamma-D-glutamyl-L-tryptophan.
authors.affiliation: Division of Integrated Life Science, Graduate School of Biostudies, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan. hideyuki@lif.kyoto-u.ac.jp
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Suzuki
authors.forename: Kenji
authors.initials: K
authors.lastname: Kato
authors.forename: Hidehiko
authors.initials: H
authors.lastname: Kumagai
mesh_terms: D004151:Dipeptides / Q000138:chemical synthesis* / Q000302:isolation & purification; D004926:Escherichia coli / Q000201:enzymology*; D005973:Glutamine / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry*; D005723:gamma-Glutamyltransferase / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D005973:Glutamine; C470075:golotimod; D014364:Tryptophan; D005723:gamma-Glutamyltransferase