title: Enantioselective N-acetylation of 2-phenylglycine by an unusual N-acetyltransferase from Chryseobacterium sp.
abstract: The demand for D-2-phenylglycine used to synthesize semisynthetic antibiotics and pesticides is increasing. We have isolated a Chryseobacterium sp. that selectively transformed the L-form of racemic D,L-2-phenylglycine to (2S)-2-acetylamide-2-phenylacetic acid with a molar yield of 50% and an enantiomer excess of >99.5% under optimal culture conditions, consequently resulting in 99% pure D-2-phenylglycine remaining in the culture. The enantioselective N-acetylation was catalyzed by an acetyl-CoA-dependent N-acetyltransferase whose synthesis was induced by L-2-phenylglycine. The enzyme differed from previously reported bacterial arylamine N-acetyltransferases in molecular mass and substrate specificity. The relative activity ratio of the enzyme with the substrates L-2-phenylglycine, D-2-phenylglycine, 2-(2-chlorophenyl)glycine, and 5-aminosalicylic acid (a good substrate of arylamine N-acetyltransferase) was 100:0:56.9:5.49, respectively. The biotransformation by the N-acetyltransferase-producing bacterium reported here could constitute a new preparative route for the enzymatic resolution of D,L-2-phenylglycine.
authors.affiliation: Department of Agrobioscience, Graduate School of Agricultural Science, Kobe University, Nada-ku, Kobe, Japan. hakko3@kobe-u.ac.jp
authors.forename: Shinji
authors.initials: S
authors.lastname: Takenaka
authors.forename: Yuuta
authors.initials: Y
authors.lastname: Honma
authors.forename: Kenji
authors.initials: K
authors.lastname: Yoshida
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yoshida
mesh_terms: D000107:Acetylation; D000123:Acetyltransferases / Q000378:metabolism*; D001711:Biotransformation; D045247:Chryseobacterium / Q000201:enzymology* / Q000235:genetics; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D005998:Glycine / Q000031:analogs & derivatives* / Q000378:metabolism; D008969:Molecular Sequence Data; D017422:Sequence Analysis, DNA
chemical_list: D004269:DNA, Bacterial; C008852:2-phenylglycine; D000123:Acetyltransferases; D005998:Glycine