title: Synthesis of homologous peptides using fragment condensation: analogs of an HIV proteinase substrate.
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.
authors.affiliation: Laboratory of Molecular Virology and Carcinogenesis, PRI/DynCorp., NCI-Frederick Cancer Research and Development Center, MD.
authors.forename: I
authors.initials: I
authors.lastname: Bláha
authors.forename: J
authors.initials: J
authors.lastname: Nemec
authors.forename: J
authors.initials: J
authors.lastname: Tözsér
authors.forename: S
authors.initials: S
authors.lastname: Oroszlan
mesh_terms: D000595:Amino Acid Sequence; D016282:Aspartic Acid Endopeptidases; D004126:Dimethylformamide / Q000737:chemistry; D016333:HIV Protease / Q000378:metabolism*; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012689:Sequence Homology, Nucleic Acid; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
chemical_list: D009842:Oligopeptides; C073771:tert-butyloxycarbonyl-valyl-benzylseryl-glutaminyl-asparaginyl-(BrZ)tyrosine; C073772:tert-butyloxycarbonyl-valyl-(benzyl)seryl-glutaminyl-asparaginyl-(BrZ)tyrosyl-proline; C073773:HIV protease nonapeptide substrate; D004126:Dimethylformamide; D016282:Aspartic Acid Endopeptidases; D016333:HIV Protease; C065184:p16 protease, Human immunodeficiency virus 2