Preparation of D-cycloserine and 13C-labeled D-cycloserine

Nathan C. Thacker; Judit Molnár-Tóth; Judy L. Miska; Raul G. Barletta; James M. Takacs

doi:10.3987/COM-12-12553

Preparation of D-cycloserine and ¹³C-labeled D-cycloserine

Nathan C. Thacker, Judit Molnár-Tóth, Judy L. Miska, Raul G. Barletta, James M. Takacs

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

2 Scopus citations

Abstract

D-Cycloserine (DCS), a second stage drug for the treatment of tuberculosis, is synthesized in 19.8% overall yield from DL-serine methyl ester. This synthetic route gives both enantiomers of cycloserine via a corrected and improved one pot resolution procedure using D- and L-tartaric acids. The route is used to synthesize a 13C-labeled derivative for use in biological studies.

Original language	English (US)
Pages (from-to)	1575-1582
Number of pages	8
Journal	Heterocycles
Volume	86
Issue number	2
DOIs	https://doi.org/10.3987/COM-12-12553
State	Published - 2012

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "D-Cycloserine (DCS), a second stage drug for the treatment of tuberculosis, is synthesized in 19.8% overall yield from DL-serine methyl ester. This synthetic route gives both enantiomers of cycloserine via a corrected and improved one pot resolution procedure using D- and L-tartaric acids. The route is used to synthesize a 13C-labeled derivative for use in biological studies.",

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AU - Thacker, Nathan C.

AU - Molnár-Tóth, Judit

AU - Miska, Judy L.

AU - Barletta, Raul G.

AU - Takacs, James M.

PY - 2012

Y1 - 2012

N2 - D-Cycloserine (DCS), a second stage drug for the treatment of tuberculosis, is synthesized in 19.8% overall yield from DL-serine methyl ester. This synthetic route gives both enantiomers of cycloserine via a corrected and improved one pot resolution procedure using D- and L-tartaric acids. The route is used to synthesize a 13C-labeled derivative for use in biological studies.

AB - D-Cycloserine (DCS), a second stage drug for the treatment of tuberculosis, is synthesized in 19.8% overall yield from DL-serine methyl ester. This synthetic route gives both enantiomers of cycloserine via a corrected and improved one pot resolution procedure using D- and L-tartaric acids. The route is used to synthesize a 13C-labeled derivative for use in biological studies.

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Preparation of D-cycloserine and ¹³C-labeled D-cycloserine

Abstract

ASJC Scopus subject areas

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