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Synthesis of deuterium and C-13-labelled ethyl glycolate and their subsequent use in the synthesis of labelled analogues of the DNA adduct O6-carboxymethyl-2′-deoxyguanosine

Moore, SA and Shuker, DEG (2011) Synthesis of deuterium and C-13-labelled ethyl glycolate and their subsequent use in the synthesis of labelled analogues of the DNA adduct O6-carboxymethyl-2′-deoxyguanosine. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 54 (14). pp. 855-858. ISSN 0362-4803

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Abstract

The adduct O6-carboxymethyl-2'-deoxyguanosine (O6CMdG) is of importance as it has been previously linked to high red meat diet in humans, and as yet, a liquid chromatography-mass spectrometry (LC-MS) method has not been developed due to lack of appropriate standards. The synthesis of the deuterated and C-13 analogues required the use of [2H2]- and [13C2]ethyl glycolate to label the carboxymethyl moiety of O6CMdG. [2H2]Ethyl glycolate was synthesised via acid hydrolysis of ethyl diazoacetate using deuterated solvents (59% yield), whilst [13C2]ethyl glycolate was synthesised from [13C2]glycine in a three-step procedure (35% yield). The labelled ethyl glycolates were then used to synthesise [2H2]- and [13C2]O6CMdG for future use as internal standards in the LC-MS analysis of biological samples. Copyright © 2011 John Wiley & Sons, Ltd.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Synthesis of deuterium and C-13-labelled ethyl glycolate and their subsequent use in the synthesis of labelled analogues of the DNA adduct O6-carboxymethyl-2'-deoxyguanosine, Journal of Labelled Compounds and Radiopharmaceuticals, v.54(14), pp.855-58, which has been published in final form at http://dx.doi.org/10.1002/jlcr.1923. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Uncontrolled Keywords: 0305 Organic Chemistry, 1115 Pharmacology And Pharmaceutical Sciences
Subjects: R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: WILEY-BLACKWELL
Related URLs:
Date Deposited: 21 May 2015 14:03
Last Modified: 08 Sep 2015 13:52
DOI or Identification number: 10.1002/jlcr.1923
URI: http://researchonline.ljmu.ac.uk/id/eprint/1148

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