Aspartic protease inhibitors: expedient synthesis of 2-substituted statines.
[reaction: see text]. General stereocontrolled synthesis of all four (2,3)-stereoisomers of 2-substituted statines is described. The 2,3-syn and 2,3-anti isomers were synthesized via beta-ketoester reduction and aldol reactions, respectively. Peptides containing 2-substituted statines inhibit porcine pepsin with nanomolar IC50 values.
Travins
J M
JM
Department of Chemistry and School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Bursavich
M G
MG
Veber
D F
DF
Rich
D H
DH
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors*; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013552:Swine
D000596:Amino Acids; D011480:Protease Inhibitors; D016282:Aspartic Acid Endopeptidases; C013165:statine