Chain Extension of Amino Acid Skeletons: Preparation of Ketomethylene Isosteres

Authors

Cory R. Theberge, University of New Hampshire
Charles K. Zercher, University of New HampshireFollow

Abstract

Ketomethylene isosteric replacements for peptide bonds were generated through a zinc carbenoid-mediated chain extension reaction in which a variety of amino acid-derived β-keto esters are converted to γ-keto esters in a single step. The reaction tolerates a variety of protecting groups and amino acid side chains with no epimerization of the amino acid stereocenter.

Department

Chemistry

Publication Date

2-24-2003

Journal Title

Tetrahedron

Publisher

Elsevier

Digital Object Identifier (DOI)

10.1016/S0040-4020(03)00052-8

Document Type

Article

Recommended Citation

Chain Extension of Amino Acid Skeletons: Preparation of Ketomethylene Isosteres, Theberge, C. R.; Zercher, C. K. Tetrahedron 2003, 59, 1521-1527.

Rights

Copyright © 2003, Elsevier