Journal
JOURNAL OF MEDICINAL CHEMISTRY
Volume 50, Issue 26, Pages 6458-6461Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jm701001c
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Funding
- NIDDK NIH HHS [DK R01 73466-01] Funding Source: Medline
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A new two-step methodology achieves stereoselective synthesis of beta-nicotinamide riboside and a series of related amide, ester, and acid nucleosides. Compounds were prepared through a triacetylated-nicotinate ester nucleoside, via coupling of either ethylnicotinate or phenylnicotinate with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose. Nicotinamide riboside, nicotinic acid riboside, O-ethyinicotinate riboside, O-methylnicotinate riboside, and several N-alkyl derivatives increased NAD(+) concentrations from 1.2-2.7-fold in several mammalian cell lines. These findings establish bioavailability and potent effects of these nucleosides in stimulating the increase of NAD(+) concentrations in mammalian cells.
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