Design and synthesis of a β-amino phosphotyrosyl mimetic suitably protected for peptide synthesis

K Lee, M Zhang, D Yang, TR Burke

Index: Lee, Kyeong; Zhang, Manchao; Yang, Dajun; Burke Jr., Terrence R. Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 23 p. 3399 - 3401

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Citation Number: 12

Abstract

Mimetics of phosphotyrosine (pTyr) such as phosphonomethylphenylalanine (Pmp) have traditionally retained α-amino functionality. However, β-amino acids represent isomeric variants, which may exhibit properties that are distinct from the parent. Reported herein is the first β-amino pTyr mimetic (Pmpβ) bearing protection suitable for peptide synthesis. Preparation of Pmpβ was accomplished enantioselectively in 43% overall yield from ...