Synthetic, three-dimensionally stabilized polypeptide mimics of

Details Synthetic, three-dimensionally stabilized polypeptide mimics of Synthetic, three-dimensionally stabilized polypeptide mimics of

1995-06-01

1998-09-15

Achutamurthy, Ponnathapura

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Cyclic peptides

530317, 530323, 5303871, C07K 754, C07K 14155

Patent

active

058079793

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 range of biologically active compounds which have stable three-dimensional structures which allow the compounds to be used to obtain, for example, stabilized three-dimensional peptides which mimic the antigenic sites on viral envelopes which are useful as vaccines.

REFERENCES:
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