Synthesis of Gemcitabine-13C, 15N2 and Gemcitabine-13C, 15N2 Metabolites

Homemade urea-13C, 15N2 was used to react with 3-methyl acrylonitrile closure to form cytosine-13C, 15N2 (2),which was protected by trimethylsilylation with BSA and condensed with 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate at 120 ℃ to afford blocked gemcitabine-13...

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Published inTong wei su Vol. 27; no. 2; pp. 82 - 86
Main Author ZHU Cheng-gu;YANG Shao-zu;YAN Sheng-wang;FANG Ning-jing;CAI Ding-long;LI Gang
Format Journal Article
LanguageChinese
Published Editorial Board of Journal of Isotopes 01.02.2014
Subjects
15N2 gemcitabine-13C
15N2 metabolites
isotope labeling synthesis gemcitabine-13C
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Summary:Homemade urea-13C, 15N2 was used to react with 3-methyl acrylonitrile closure to form cytosine-13C, 15N2 (2),which was protected by trimethylsilylation with BSA and condensed with 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate at 120 ℃ to afford blocked gemcitabine-13C, 15N2. Hydrolytic removal of the blocking groups of gemcitabine-13C, 15N2 with NaOH gave gemcitabine-13C, 15N2, and its metabolite was obtained by further hydrolytic deamination of gemcitabine-13C, 15N2. The final products were characterized and detected by HPLC, LC-MS and NMR, and confirmed that the chemical purities were higher than 98%, isotopic abundances were 99% 13C, 98% 15N, and they were suitable for drug metabolism studies.
ISSN:1000-7512
1000-7512
DOI:10.7538/tws.2014.27.02.0082