Poststatin, a new inhibitor of prolyl endopeptidase. III. Optical resolution of 3-amino-2-hydroxyvaleric acid and absolute configuration of poststatin.
3-Amino-2-hydroxyvaleric acid was prepared, and separated into its diastereomers. The relative stereochemistry was determined by 1H NMR in their oxazolidone derivatives. The threo-isomer was resolved by (S)-1-(1-naphthyl) ethylamine in the N-(p-methoxybenzyloxycarbonyl) derivative. The absolute configuration of (--)-threo-3-(p-methoxybenzyloxycarbonyl)amino-2-hydroxyvaleric acid was confirmed to be 2R, 3S. The absolute configuration of 3-amino-2- oxovaleric acid in poststatin was confirmed to be S by comparison of the four stereoisomers of methyl N, O-bis(3,5-dinitrobenzoyl)-3-amino-2-hydroxyvalerate derived from 3-amino-2-hydroxyvaleric acid and that derived from 3-amino-2-oxovaleryl moiety of poststatin by means of HPLC with chiral column.
Tsuda
M
M
Institute of Microbial Chemistry, M.C.R.F., Tokyo, Japan.
Muraoka
Y
Y
Nagai
M
M
Aoyagi
T
T
Takeuchi
T
T
D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000085822:Prolyl Oligopeptidases; D011487:Protein Conformation; D012697:Serine Endopeptidases / Q000378:metabolism*; D015842:Serine Proteinase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism
D009842:Oligopeptides; D015842:Serine Proteinase Inhibitors; C071400:poststatin; D012697:Serine Endopeptidases; D000085822:Prolyl Oligopeptidases