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US 5,440,013 AGranted
Conformationally restricted mimetics of beta turns and beta bulges and peptides containing the same
AssigneeThe Board of Trustees of the University of Illinois
InventorMichael Kahn
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Abstract
The invention provides materials and methods for synthesizing novel beta-turn mimetics, as well as the novel beta-turn mimetics themselves, and peptides containing the same. Also provided are novel synthetic nonpeptide therapeutic molecules designed upon the interactions between beta-turn mimetics or peptides containing the same, and receptors or enzymes.
Claims8
A method for making a beta-turn mimetic having the structure ##STR20## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and Z are as identified below, comprising:
- (a) coupling a first modular component piece to a second modular component piece to yield a nascent beta-turn mimetic, wherein the first modular component piece has the structure:
- ##STR21## where R.sup.4 is a naturally-occurring amino acid side chain substituent or analog thereof, P is a protective group suitable for use in peptide synthesis, and X is a linker moiety terminating in an amino or hydrazino group;
- and wherein the second modular component piece has the structure:
- ##STR22## where R.sup.3 is a naturally-occurring amino acid side chain substituent or analog thereof, and P is a protective group suitable for use in peptide synthesis;
- (b) coupling a third modular component piece to the nascent beta-turn mimetic to yield a pre-cyclized beta-turn mimetic, wherein the third modular component piece is selected from the structures:
- ##STR23## where R.sup.1 and R.sup.2 are naturally occurring amino acid side chain substituents or analogs thereof, Z is hydrogen or --CH.sub.3 and P is a protective group suitable for use in peptide synthesis;
- and
- (c) cyclizing the pre-cyclized reverse-turn mimetic to yield the beta-turn mimetic.
5 more elements
Dependencies are inferred from the claim text.