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Synthesis of 13 C‐labeled 5‐aminoimidazole‐4‐carboxamide‐1‐β‐D‐[ 13 C 5 ] ribofuranosyl 5′‐monophosphate
Author(s) -
Zarkin Allison K.,
Elkins Phyllis D.,
Gilbert Amanda,
Jester Teresa L.,
Seltzman Herbert H.
Publication year - 2018
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3647
Subject(s) - chemistry , inosine , ribose , carboxamide , metabolite , stereochemistry , imp dehydrogenase , riboside , cleavage (geology) , adenosine monophosphate , yield (engineering) , ribonucleoside , adenosine , nucleotide , enzyme , rna , biochemistry , medicine , transplantation , geotechnical engineering , fracture (geology) , engineering , mycophenolic acid , gene , materials science , surgery , metallurgy
5‐Aminoimidazole‐4‐carboxamide‐1‐β‐D‐[ 13 C 5 ] ribofuranosyl 5′‐monophosphate ([ 13 C 5 ribose] AICAR‐PO 3 H 2 ) ( 6 ) has been synthesized from [ 13 C 5 ]adenosine. Incorporation of the mass‐label into [ 13 C 5 ribose] AICAR‐PO 3 H 2 provides a useful standard to aid in metabolite identification and quantification in monitoring metabolic pathways. A synthetic route to the 13 C‐labeled compound has not been previously reported. Our method employs a hybrid enzymatic, and chemical synthesis approach that applies an enzymatic conversion from adenosine to inosine followed by a ring‐cleavage of the protected inosine. A direct phosphorylation of the resulting 2′,3′‐isopropylidine acadesine ( 5 ) was developed to yield the title compound in 99% purity following ion exchange chromatography.