title: The use of cystathionine gamma-synthase in the production of alpha and chiral beta deuterated amino acids.
abstract: Chiral exchange at the alpha hydrogen position can be carried out on gram scale in 2H2O for all of the standard amino acids utilizing Escherichia coli cystathionine gamma-synthase. The alpha hydrogen exchange of glycine is highly stereoselective. The amino acids fall into four classes with respect to the selectivity of exchange at the beta position: beta'/beta rate approximately 50 (arginine, glutamine, histidine, homoserine, and lysine), beta'/beta rate approximately 8 (asparagine, glutamate, methionine, ornithine, and S-methyl cysteine), beta'/beta approximately 1 (leucine, aspartate, and alanine), and those seemingly too slow for large-scale exchange (isoleucine, phenylalanine, O-methyl tyrosine, serine, threonine, tryptophan, and valine). The stereochemistry of selective beta exchange is the same for all cases studied.
authors.affiliation: Department of Biochemistry, Northwestern University, Evanston, Illinois 60208.
authors.forename: R J
authors.initials: RJ
authors.lastname: Homer
authors.forename: M S
authors.initials: MS
authors.lastname: Kim
authors.forename: D M
authors.initials: DM
authors.lastname: LeMaster
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D019757:Carbon-Oxygen Lyases; D003903:Deuterium / Q000737:chemistry; D004926:Escherichia coli / Q000201:enzymology; D008190:Lyases / Q000737:chemistry* / Q000235:genetics; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003903:Deuterium; C022696:O-succinylhomoserine (thiol)-lyase; D008190:Lyases; D019757:Carbon-Oxygen Lyases