Stereoselective synthesis of nicotinamide β-riboside and nucleoside analogs

A stereoselective synthesis of β-anomers of nicotinamide riboside (NAR), its deamidated analog (NaR), and of a nicotinamide C-methylated riboside derivative (NA3′- C-MeR) was developed. The β-anomers of N-ribofuranosylnicotine-3-carboxamide (β-NAR) and its nicotinic acid analog (β-NaR) were obtained...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-09, Vol.14 (18), p.4655-4658
Main Authors: Franchetti, Palmarisa, Pasqualini, Michela, Petrelli, Riccardo, Ricciutelli, Massimo, Vita, Patrizia, Cappellacci, Loredana
Format: Article
Language:English
Subjects:
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Glycosylation
NAD
Niacinamide - analogs & derivatives
Niacinamide - chemical synthesis
Niacinamide - chemistry
Nicotinamide β-riboside
Nicotinic acid β-riboside
Nucleosides - chemical synthesis
Nucleosides - chemistry
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:A stereoselective synthesis of β-anomers of nicotinamide riboside (NAR), its deamidated analog (NaR), and of a nicotinamide C-methylated riboside derivative (NA3′- C-MeR) was developed. The β-anomers of N-ribofuranosylnicotine-3-carboxamide (β-NAR) and its nicotinic acid analog (β-NaR) were obtained by stereoselective synthesis via glycosylation of the presilylated bases under Vorbruggen’s protocol. A NAR analog, methylated in position 3 of the ribosylic moiety, is also reported.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.06.093