Synthesis and structure of the glutathione conjugate of chloroacetaldehyde

Yushun Li; Dean E. Carter; Eugene A. Mash

doi:10.1081/SCC-120004149

Synthesis and structure of the glutathione conjugate of chloroacetaldehyde

Yushun Li
, Dean E. Carter
, Eugene A. Mash

Chemistry and Biochemistry

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

5 Scopus citations

Abstract

A synthesis and the structure of the title compound are presented. The sodium salt of N-BOC glutathione dimethyl ester was S-alkylated with chloroacetaldehyde. Following a protection/deprotection sequence, condensation of the aldehyde moiety with the nitrogen of the cysteine residue and subsequent dehydration produced a glutathione derivative that contains a 2,3-dihydro-4H-1,4-thiazine ring.

Original language	English (US)
Pages (from-to)	1579-1583
Number of pages	5
Journal	Synthetic Communications
Volume	32
Issue number	10
DOIs	https://doi.org/10.1081/SCC-120004149
State	Published - 2002

Keywords

Alkylation
Chloroacetaldehyde
Glutathione
Xenobiotic

ASJC Scopus subject areas

Organic Chemistry

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10.1081/SCC-120004149

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title = "Synthesis and structure of the glutathione conjugate of chloroacetaldehyde",

abstract = "A synthesis and the structure of the title compound are presented. The sodium salt of N-BOC glutathione dimethyl ester was S-alkylated with chloroacetaldehyde. Following a protection/deprotection sequence, condensation of the aldehyde moiety with the nitrogen of the cysteine residue and subsequent dehydration produced a glutathione derivative that contains a 2,3-dihydro-4H-1,4-thiazine ring.",

keywords = "Alkylation, Chloroacetaldehyde, Glutathione, Xenobiotic",

author = "Yushun Li and Carter, \{Dean E.\} and Mash, \{Eugene A.\}",

note = "Funding Information: This material is based upon work supported by NIEHS under award number ES06694.",

year = "2002",

doi = "10.1081/SCC-120004149",

language = "English (US)",

volume = "32",

pages = "1579--1583",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "10",

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TY - JOUR

T1 - Synthesis and structure of the glutathione conjugate of chloroacetaldehyde

AU - Li, Yushun

AU - Carter, Dean E.

AU - Mash, Eugene A.

N1 - Funding Information: This material is based upon work supported by NIEHS under award number ES06694.

PY - 2002

Y1 - 2002

N2 - A synthesis and the structure of the title compound are presented. The sodium salt of N-BOC glutathione dimethyl ester was S-alkylated with chloroacetaldehyde. Following a protection/deprotection sequence, condensation of the aldehyde moiety with the nitrogen of the cysteine residue and subsequent dehydration produced a glutathione derivative that contains a 2,3-dihydro-4H-1,4-thiazine ring.

AB - A synthesis and the structure of the title compound are presented. The sodium salt of N-BOC glutathione dimethyl ester was S-alkylated with chloroacetaldehyde. Following a protection/deprotection sequence, condensation of the aldehyde moiety with the nitrogen of the cysteine residue and subsequent dehydration produced a glutathione derivative that contains a 2,3-dihydro-4H-1,4-thiazine ring.

KW - Alkylation

KW - Chloroacetaldehyde

KW - Glutathione

KW - Xenobiotic

UR - https://www.scopus.com/pages/publications/0036274046

UR - https://www.scopus.com/pages/publications/0036274046#tab=citedBy

U2 - 10.1081/SCC-120004149

DO - 10.1081/SCC-120004149

M3 - Article

AN - SCOPUS:0036274046

SN - 0039-7911

VL - 32

SP - 1579

EP - 1583

JO - Synthetic Communications

JF - Synthetic Communications

IS - 10

ER -

Synthesis and structure of the glutathione conjugate of chloroacetaldehyde

Abstract

Keywords

ASJC Scopus subject areas

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