First stereoselective synthesis of an optically pure β-substituted histidine: (2s,3s)-β-methylhistidine

Sihe Wang; Xuejun Tang; Victor J. Hruby

doi:10.1016/S0040-4039(99)02223-6

First stereoselective synthesis of an optically pure β-substituted histidine: (2s,3s)-β-methylhistidine

Sihe Wang
, Xuejun Tang
, Victor J. Hruby

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

20 Scopus citations

Abstract

We report the first example of the asymmetric synthesis of the β- substituted histidine, (2S,3S)-β-methylhistidine. A key in the synthesis is the use of the protecting group, 2-mesitylenesulfonyl (Mts-), for the imidazole ring to minimize epimerization during synthesis. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	1307-1310
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(99)02223-6
State	Published - Feb 26 2000
Externally published	Yes

Keywords

Amino acids
Asymmetric synthesis
Chiral auxiliary
Mesitylenesulfonyl
β-substituted histidine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)02223-6

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abstract = "We report the first example of the asymmetric synthesis of the β- substituted histidine, (2S,3S)-β-methylhistidine. A key in the synthesis is the use of the protecting group, 2-mesitylenesulfonyl (Mts-), for the imidazole ring to minimize epimerization during synthesis. (C) 2000 Elsevier Science Ltd.",

keywords = "Amino acids, Asymmetric synthesis, Chiral auxiliary, Mesitylenesulfonyl, β-substituted histidine",

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T1 - First stereoselective synthesis of an optically pure β-substituted histidine

T2 - (2s,3s)-β-methylhistidine

AU - Wang, Sihe

AU - Tang, Xuejun

AU - Hruby, Victor J.

PY - 2000/2/26

Y1 - 2000/2/26

N2 - We report the first example of the asymmetric synthesis of the β- substituted histidine, (2S,3S)-β-methylhistidine. A key in the synthesis is the use of the protecting group, 2-mesitylenesulfonyl (Mts-), for the imidazole ring to minimize epimerization during synthesis. (C) 2000 Elsevier Science Ltd.

AB - We report the first example of the asymmetric synthesis of the β- substituted histidine, (2S,3S)-β-methylhistidine. A key in the synthesis is the use of the protecting group, 2-mesitylenesulfonyl (Mts-), for the imidazole ring to minimize epimerization during synthesis. (C) 2000 Elsevier Science Ltd.

KW - Amino acids

KW - Asymmetric synthesis

KW - Chiral auxiliary

KW - Mesitylenesulfonyl

KW - β-substituted histidine

UR - https://www.scopus.com/pages/publications/0034716521

UR - https://www.scopus.com/pages/publications/0034716521#tab=citedBy

U2 - 10.1016/S0040-4039(99)02223-6

DO - 10.1016/S0040-4039(99)02223-6

M3 - Article

AN - SCOPUS:0034716521

SN - 0040-4039

VL - 41

SP - 1307

EP - 1310

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

First stereoselective synthesis of an optically pure β-substituted histidine: (2s,3s)-β-methylhistidine

Abstract

Keywords

ASJC Scopus subject areas

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