The use of cystathionine gamma-synthase in the production of alpha and chiral beta deuterated amino acids.
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.
Homer
R J
RJ
Department of Biochemistry, Northwestern University, Evanston, Illinois 60208.
Kim
M S
MS
LeMaster
D M
DM
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
D000596:Amino Acids; D003903:Deuterium; C022696:O-succinylhomoserine (thiol)-lyase; D008190:Lyases; D019757:Carbon-Oxygen Lyases