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

✍ Scribed by Sharon A. Moore; David E. G. Shuker

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: French
• Weight: 151 KB
• Volume: 54
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.1923

✦ Synopsis

The adduct O^6^‐carboxymethyl‐2′‐deoxyguanosine (O^6^CMdG) 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 [^2^H~2~]‐ and [^13^C~2~]ethyl glycolate to label the carboxymethyl moiety of O^6^CMdG. [^2^H~2~]Ethyl glycolate was synthesised via acid hydrolysis of ethyl diazoacetate using deuterated solvents (59% yield), whilst [^13^C~2~]ethyl glycolate was synthesised from [^13^C~2~]glycine in a three‐step procedure (35% yield). The labelled ethyl glycolates were then used to synthesise [^2^H~2~]‐ and [^13^C~2~]O^6^CMdG for future use as internal standards in the LC‐MS analysis of biological samples. Copyright © 2011 John Wiley & Sons, Ltd.