Synthetic, three-dimensionally stabilized polypeptide mimics of HIV

US5807979A · kind A · utility

Assignee

• THE SCRIPPS RESEARCH INSTITUTE · US

Inventors

• Arnold Satterthwait · Del Mar, US
• Thomas Arrhenius · Del Mar, US
• Lin-Chang Chiang · Export, US
• Edelmira Cabezas · Sunnyvale, US

Key dates

• Filing date: Jun 1, 1995
• Grant date: Sep 15, 1998
• Expiry date: Jun 1, 2015

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02A50/30
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Methods for synthesizing three-dimensional stabilized peptides which mimic the three-dimensional configuration of the active site of a natural, biologically active protein are carried out by (1) noting the three-dimensional configuration of the active site of a known biologically active protein (2) noting the amino acid sequence and the hydrogen bonds existing between amino acids which hydrogen bonds are capable of maintaining the three-dimensional configuration of the active site and (3) producing a synthetic three-dimensional peptide to mimic the structure of the active site. The synthetic peptide is synthesized so as to have the same or a similar amino acid sequence to the amino acid sequence of the active site of the biologically active polypeptide but with the stabilizing hydrogen bonds being replaced by a bridging divalent radical selected from the group of --(N)--C(CH.sub.3).dbd.N(H.sup.+)--CH.sub.2 --(N)--; --(N)--C(CH.sub.3).dbd.N(H.sup.+)--CH.sub.2 --CH.sub.2 --(N)--; and --(N)--N.dbd.CH--CH.sub.2 --CH.sub.2 --CH.sub.2 --(C)--. The stabilized three-dimensional peptide obtained is then isolated from the reaction mixture. The invention makes it possible to produce a wide ra…