Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d 2).
Beilstein J Org Chem, 2022;18:1466-1470.
Turhanen PA[1]
Affiliations
PMID: 36300010DOI: 10.3762/bjoc.18.153
Impact factor: 2.544
Abstract
The chemical synthesis of the dideuterium-labelled ATP analogue 1-adenosin-5'-yl-3-(3-methylbut-3-en-1,1-d 2-1-ol) triphosphoric acid diester (ApppI(d 2)) is described. ApppI has been reported to be an important mevalonate pathway metabolite, induced by nitrogen-containing bisphosphonates used for the treatment of several diseases related to the calcium metabolism, of which osteoporosis is the most well-known. The availability of ApppI(d 2) opens possibilities to quantitative measurements of ApppI in biological samples by mass spectrometry. The synthesized target compound ApppI(d 2) was purified by high-performance counter current chromatography and characterized by 1H, 13C, and 31P NMR spectroscopy as well as high-resolution mass spectrometry.
Keywords: ATP; ApppI; HPCCC; NMR; deuterium labelling; mevalonate pathway; synthesis
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