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Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d ₂).

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.

SUBMITTER: Turhanen PA

PROVIDER: S-EPMC9577381 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d 2).

Turhanen Petri A PA

Beilstein journal of organic chemistry 20221014

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) o ...[more]

PMID: 36300010

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