Syntheses of Nicotinamide Riboside and Derivatives: Effective Agents for Increasing Nicotinamide Adenine Dinucleotide Concentrations in Mammalian Cells

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• 作者：Tianle Yang ; Noel Yan-Ki Chan ; Anthony A. Sauve
• 刊名：Journal of Medicinal Chemistry
• 出版年：2007
• 出版时间：December 27, 2007
• 年：2007
• 卷：50
• 期：26
• 页码：6458 - 6461
• 全文大小：90K
• 年卷期：v.50,no.26(December 27, 2007)
• ISSN：1520-4804

文摘

A new two-step methodology achieves stereoselective synthesis of β-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-β-D-ribofuranose. Nicotinamide riboside, nicotinic acid riboside, O-ethylnicotinate 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.