Poststatin, a new inhibitor of prolyl endopeptidase. IV. The chemical synthesis of poststain.
Total synthesis of poststatin was achieved by both liquid phase and solid phase methods. In both methods, the (2R,3S)-3-amino-2-hydroxyvaleric acid moiety was incorporated into protected pentapeptides, and was oxidized to (S)-3-amino-2-oxovaleric acid (postine). Deprotection of the oxidized pentapeptides gave a specimen identical with natural poststatin in physico-chemical properties and prolyl endopeptidase inhibitory activity.
Tsuda
M
M
Institute of Microbial Chemistry, M. C. R. F., Tokyo, Japan.
Muraoka
Y
Y
Nagai
M
M
Takeuchi
T
T
Aoyagi
T
T
D000595:Amino Acid Sequence; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000085822:Prolyl Oligopeptidases; D012697:Serine Endopeptidases / Q000378:metabolism*; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D009842:Oligopeptides; D015842:Serine Proteinase Inhibitors; C071400:poststatin; D012697:Serine Endopeptidases; D000085822:Prolyl Oligopeptidases