Work

Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in β-Strand Peptidomimetics

Year: 2007

Type: article

Abstract: The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. beta-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo062664i

Authors: Ming C. Hammond, Paul A. Bartlett

Institution: University of California, Berkeley

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: DESIGN AND SYNTHESIS OF PEPTIDE MIMICS, G2142624103, STUDIES IN THE SHIKIMATE-CHORISMATE PATHWAY