Synthesis of all the stereoisomers of statine (4-amino-3-hydroxy-6-methylheptanoic acid). Inhibition of pepsin activity by N-carbobenzoxy-L-valyl-L-valyl-statine derived from the four stereoisomers

J Med Chem. 1979 May;22(5):577-9. doi: 10.1021/jm00191a023.

Abstract

Synthesis of all four stereoisomers of the novel amino acid statine, 4-amino-3-hydroxy-6-methylheptanoic acid, found in pepstatin, a potent acid protease inhibitor, has been accomplished. Carbobenzoxy-L-valyl-L-valyl-statine tripeptides derived from all four stereoisomers have been prepared and their effect on pepsin activity is compared to that of pepstatin.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / pharmacology
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / pharmacology
  • Hemoglobins / metabolism
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacology
  • Pepsin A / antagonists & inhibitors*
  • Pepstatins / pharmacology
  • Stereoisomerism

Substances

  • Amino Acids
  • Amino Alcohols
  • Hemoglobins
  • Oligopeptides
  • Pepstatins
  • Pepsin A