title: The synthesis of (14)C-labeled, (13)CD2-labeled saxagliptin, and its (13)CD2-labeled 5-hydroxy metabolite.
abstract: (14)C-labeled saxagliptin, (13) CD2-labeled saxagliptin, and its (13) CD2-labeled 5-hydroxy metabolite were synthesized to further support development of the compound for biological studies. This paper describes new syntheses leading to the desired compounds. A total of 3.0 mCi of (14)C-labeled saxagliptin was obtained with a specific activity of 53.98 μCi/mg (17.13 mCi/mmol). The radiochemical purity determined by HPLC was 99.29%, and the overall radiochemical yield was 3.0% based upon 100 mCi of [(14)C]CH2 I2 starting material. By following similar synthetic routes, 580.0 mg of (13)CD2-labeled saxagliptin and 153.1 mg of (13)CD2-labeled 5-hydroxysaxagliptin metabolite were prepared.
authors: Department of Chemical Synthesis, Radiochemistry Group, Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research and Development, P.O. Box 4000, Princeton, NJ, 08543, USA.
authors: Scott B
authors: SB
authors: Tran
authors: Brad D
authors: BD
authors: Maxwell
authors: Kai
authors: K
authors: Cao
authors: Samuel J
authors: SJ
authors: Bonacorsi
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D002247:Carbon Isotopes / Q000737:chemistry; D002250:Carbon Radioisotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
chemical_list: C558749:5-hydroxysaxagliptin; D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D004151:Dipeptides; C502994:saxagliptin; D000218:Adamantane
keywords: 13C-label; 14C-label; deuterium; isotope labeling; saxagliptin; type 2 diabetes