Synthesis of homologous peptides using fragment condensation: analogs of an HIV proteinase substrate

Int J Pept Protein Res. 1991 Nov;38(5):453-8. doi: 10.1111/j.1399-3011.1991.tb01526.x.

Abstract

Two protected peptides Boc-Val-Ser(Bzl)-Gln-Asn-Tyr(BrZ)OH and Boc-Val-Ser(Bzl)-Gln-Asn-Tyr(BrZ)-ProOH were synthesized on a resin substituted by 9-(hydroxymethyl)-2-fluoreneacetic acid. After cleavage with piperidine/DMF, desalting, and activation, these peptides were used for the synthesis of 11 analogs of an HIV proteinase nonapeptide substrate Val-Ser-Gln-Asn-Tyr-Pro-Ile-Val-Gln-NH2 using fragment condensation in solid phase. The fragment condensation was made in an ultrasonic bath. Using only 2 equivalents of the activated peptide in a DMF solution, this reaction was complete in 2 h. All nonapeptides were assayed as substrates for HIV-1 and HIV-2 proteinases.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Aspartic Acid Endopeptidases
  • Dimethylformamide / chemistry
  • HIV Protease / metabolism*
  • Molecular Sequence Data
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / metabolism
  • Sequence Homology, Nucleic Acid
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Oligopeptides
  • tert-butyloxycarbonyl-valyl-benzylseryl-glutaminyl-asparaginyl-(BrZ)tyrosine
  • tert-butyloxycarbonyl-valyl-(benzyl)seryl-glutaminyl-asparaginyl-(BrZ)tyrosyl-proline
  • HIV protease nonapeptide substrate
  • Dimethylformamide
  • Aspartic Acid Endopeptidases
  • HIV Protease
  • p16 protease, Human immunodeficiency virus 2