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

Kyeong Lee; Manchao Zhang; Dajun Yang; Terrence R. Burke

doi:10.1016/S0960-894X(02)00783-7

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

Kyeong Lee, Manchao Zhang, Dajun Yang, Terrence R. Burke

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

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 (Pmp_β) bearing protection suitable for peptide synthesis. Preparation of Pmp_β was accomplished enantioselectively in 43% overall yield from commercially available 4-vinylbenzyl chloride.

Original language	English
Pages (from-to)	3399-3401
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	12
Issue number	23
DOIs	https://doi.org/10.1016/S0960-894X(02)00783-7
State	Published - Dec 2002

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title = "Design and synthesis of a β-amino phosphotyrosyl mimetic suitably protected for peptide synthesis",

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 commercially available 4-vinylbenzyl chloride.",

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AU - Lee, Kyeong

AU - Zhang, Manchao

AU - Yang, Dajun

AU - Burke, Terrence R.

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N2 - 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 commercially available 4-vinylbenzyl chloride.

AB - 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 commercially available 4-vinylbenzyl chloride.

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U2 - 10.1016/S0960-894X(02)00783-7

DO - 10.1016/S0960-894X(02)00783-7

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SN - 0960-894X

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

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

Abstract

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