An expedient synthesis of N(alpha)-protected-L-tetrahydrofuranylglycine and its application in the synthesis of novel substrate based inhibitors of HIV-1 protease

Bioorg Med Chem Lett. 2002 Dec 16;12(24):3615-7. doi: 10.1016/s0960-894x(02)00781-3.

Abstract

Z- and Fmoc-L-tetrahydrofuranylglycines have been obtained from L-vinylglycine through dipolar cycloaddition reaction, and its Fmoc derivative has been applied in the synthesis of modified S9 and S10 substrates of HIV-1 protease. These compounds mostly acted as strong inhibitors, rather than substrates, of the protease, probably due to the favourable interactions of the tetrahydrofuranylglycine moiety at the S(2) site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Furans / chemistry
  • Furans / pharmacology
  • Glycine / chemistry
  • Glycine / pharmacology
  • HIV Protease / metabolism
  • HIV Protease Inhibitors / chemical synthesis*
  • HIV Protease Inhibitors / pharmacology
  • Humans
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacology
  • Structure-Activity Relationship

Substances

  • Furans
  • HIV Protease Inhibitors
  • Oligopeptides
  • HIV Protease
  • Glycine