Design and synthesis of a beta-amino phosphotyrosyl mimetic suitably protected for peptide synthesis.
Mimetics of phosphotyrosine (pTyr) such as phosphonomethylphenylalanine (Pmp) have traditionally retained alpha-amino functionality. However, beta-amino acids represent isomeric variants, which may exhibit properties that are distinct from the parent. Reported herein is the first beta-amino pTyr mimetic (Pmp(beta)) bearing protection suitable for peptide synthesis. Preparation of Pmp(beta) was accomplished enantioselectively in 43% overall yield from commercially available 4-vinylbenzyl chloride.
Lee
Kyeong
K
Laboratory of Medicinal Chemistry, Center for Cancer Research, NCI-Frederick, National Institutes of Health, Frederick, MD 21702, USA.
Zhang
Manchao
M
Yang
Dajun
D
Burke
Terrence R
TR
D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry*; D003198:Computer Simulation; D008958:Models, Molecular; D010455:Peptides / Q000138:chemical synthesis*; D010649:Phenylalanine / Q000031:analogs & derivatives*; D019000:Phosphotyrosine / Q000737:chemistry*; D013237:Stereoisomerism; D018909:src Homology Domains / Q000187:drug effects
D010455:Peptides; D019000:Phosphotyrosine; D010649:Phenylalanine