Synthesis and purification of racemic 2-(1-hydroxyethyl)thiamine revisited

James T. Stivers; Michael W. Washabaugh

doi:10.1016/0045-2068(90)90025-Z

Synthesis and purification of racemic 2-(1-hydroxyethyl)thiamine revisited

James T. Stivers, Michael W. Washabaugh

School of Medicine

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

6 Scopus citations

Abstract

A procedure is reported for the rapid (≤1 day) and reproducible purification of 2-(1-hydroxyethyl)thiamine (HET) from contaminating thiamine (≤50%) using aqueous cation exchange chromatography. The unhydrated product contains ≤0.2% thiamine on the basis of its ¹H NMR spectrum, visualization on silica gel TLC by fluorescence quenching after development in 60% aqueous ethanol, and the failure to observe the hydrolysis of thiamine using an iodine trapping assay under conditions where hydrolysis of ≤0.2% contaminating thiamine would have been detected. This purification procedure is also applicable to the resolved R and S stereoisomers of HET. Several literature procedures for the synthesis and purification of racemic HET are discussed and critically evaluated.

Original language	English (US)
Pages (from-to)	425-434
Number of pages	10
Journal	Bioorganic Chemistry
Volume	18
Issue number	4
DOIs	https://doi.org/10.1016/0045-2068(90)90025-Z
State	Published - Dec 1990

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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10.1016/0045-2068(90)90025-Z

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@article{60f4b3fdc4da45378098aca0bd9861b6,

title = "Synthesis and purification of racemic 2-(1-hydroxyethyl)thiamine revisited",

abstract = "A procedure is reported for the rapid (≤1 day) and reproducible purification of 2-(1-hydroxyethyl)thiamine (HET) from contaminating thiamine (≤50%) using aqueous cation exchange chromatography. The unhydrated product contains ≤0.2% thiamine on the basis of its 1H NMR spectrum, visualization on silica gel TLC by fluorescence quenching after development in 60% aqueous ethanol, and the failure to observe the hydrolysis of thiamine using an iodine trapping assay under conditions where hydrolysis of ≤0.2% contaminating thiamine would have been detected. This purification procedure is also applicable to the resolved R and S stereoisomers of HET. Several literature procedures for the synthesis and purification of racemic HET are discussed and critically evaluated.",

author = "Stivers, {James T.} and Washabaugh, {Michael W.}",

note = "Funding Information: {\textquoteright} This research was supported in part by grants from the National Institutes of Health (GM-42878) and the American Cancer Society (JFRA-213), and a Biomedical Research Support Grant to Johns Hopkins University (2SO7RRO5445). Support was provided for J.T.S. by a National Institutes of Health Training Grant (5T32ES-07141). 2 To whom correspondence should be addressed. 3 Abbreviations used: TDP, thiamine diphosphate; HET, 2-(l-hydroxyethyl)thiamine; HETDP, 2-(1-hydroxyethyl)thiamine diphosphate; T, thiamine. 425",

year = "1990",

month = dec,

doi = "10.1016/0045-2068(90)90025-Z",

language = "English (US)",

volume = "18",

pages = "425--434",

journal = "Bioorganic Chemistry",

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publisher = "Academic Press Inc.",

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TY - JOUR

T1 - Synthesis and purification of racemic 2-(1-hydroxyethyl)thiamine revisited

AU - Stivers, James T.

AU - Washabaugh, Michael W.

N1 - Funding Information: ’ This research was supported in part by grants from the National Institutes of Health (GM-42878) and the American Cancer Society (JFRA-213), and a Biomedical Research Support Grant to Johns Hopkins University (2SO7RRO5445). Support was provided for J.T.S. by a National Institutes of Health Training Grant (5T32ES-07141). 2 To whom correspondence should be addressed. 3 Abbreviations used: TDP, thiamine diphosphate; HET, 2-(l-hydroxyethyl)thiamine; HETDP, 2-(1-hydroxyethyl)thiamine diphosphate; T, thiamine. 425

PY - 1990/12

Y1 - 1990/12

N2 - A procedure is reported for the rapid (≤1 day) and reproducible purification of 2-(1-hydroxyethyl)thiamine (HET) from contaminating thiamine (≤50%) using aqueous cation exchange chromatography. The unhydrated product contains ≤0.2% thiamine on the basis of its 1H NMR spectrum, visualization on silica gel TLC by fluorescence quenching after development in 60% aqueous ethanol, and the failure to observe the hydrolysis of thiamine using an iodine trapping assay under conditions where hydrolysis of ≤0.2% contaminating thiamine would have been detected. This purification procedure is also applicable to the resolved R and S stereoisomers of HET. Several literature procedures for the synthesis and purification of racemic HET are discussed and critically evaluated.

AB - A procedure is reported for the rapid (≤1 day) and reproducible purification of 2-(1-hydroxyethyl)thiamine (HET) from contaminating thiamine (≤50%) using aqueous cation exchange chromatography. The unhydrated product contains ≤0.2% thiamine on the basis of its 1H NMR spectrum, visualization on silica gel TLC by fluorescence quenching after development in 60% aqueous ethanol, and the failure to observe the hydrolysis of thiamine using an iodine trapping assay under conditions where hydrolysis of ≤0.2% contaminating thiamine would have been detected. This purification procedure is also applicable to the resolved R and S stereoisomers of HET. Several literature procedures for the synthesis and purification of racemic HET are discussed and critically evaluated.

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DO - 10.1016/0045-2068(90)90025-Z

M3 - Article

AN - SCOPUS:27244462380

SN - 0045-2068

VL - 18

SP - 425

EP - 434

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

IS - 4

ER -

Synthesis and purification of racemic 2-(1-hydroxyethyl)thiamine revisited

Abstract

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