Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

• Mikhail V. Makarov Marie E. Migaud Mitchell Cancer Institute, University of South Alabama, 1660 Springhill Ave., Mobile, AL 36604, USA 10.3762/bjoc.15.36 Abstract The β-anomeric form of nicotinamide riboside (NR+) is a precursor for nicotinamide adenine dinucleotide (NAD+), a redox cofactor

• modifications which have been undertaken on the nicotinoyl riboside scaffold. Keywords: anomers; glycosylation; isotopologues; isotopomeres; nicotinamide riboside; Review 1. Introduction 1-(β-D-Ribofuranosyl)nicotinamide (also referred to as nicotinamide riboside, NR+) is one of the multiple precursors of

• . 2. Synthesis of β-nicotinamide riboside Most synthetic routes to nicotinamide riboside salt forms (NR+X−) may be subdivided into two main categories (Figure 2). One is via a reaction between nicotinamide (Nam) or its analogues or derivatives A and a peracylated (halo)-D-ribofuranose B resulting in

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• mills [46][47]. Reaction scales up to 40 g were described and the conditions developed enabled exclusive formation of the β-anomer of nicotinamide riboside (NR) in the absence of toxic bromide salts. Preparation and reactions of nucleotides and their analogues Phosphorylation of NR on gram-scales using

• in a MBM. Thiolate displacement reactions of nucleoside derivatives in a MBM. Selenocyanate displacement reactions of nucleoside derivatives in a MBM. Nucleobase glycosidation reactions and subsequent deacetylation performed in a MBM. Regioselective phosphorylation of nicotinamide riboside in a MBM