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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
- 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
Graphical Abstract
Figure 1: Structural formulas of Nam, NA, NR+, NMN, and NAD+.
Figure 2: Main synthetic routes to nicotinamide riboside (NR+X−).
Scheme 1: Synthesis of NR+Cl− based on the reaction of peracylated chlorosugars with Nam.
Figure 3: Predominant formation of β-anomer over α-anomer of NR+X−.
Scheme 2: Synthesis of NR+Cl− by reacting 3,5-di-O-benzoyl-D-ribofuranosyl chloride (5) with Nam (1a).
Figure 4: Mechanism of the formation of the β-anomer of the glycosylated product in the case of the reaction ...
Scheme 3: Synthesis of NR+Br− by reacting bromosugars with Nam (1a).
Scheme 4: Synthesis of NR+OTf− based on the glycosylation of Nam (1a) with tetra-O-acetyl-β-D-ribofuranose (2a...
Scheme 5: Improved synthesis of NR+OTfˉ and NAR+OTfˉ based on the glycosylation of pre-silylated Nam or NA wi...
Scheme 6: Synthesis of triacetylated NAR+OTf− by glycosylation of nicotinic acid trimethylsilyl ester with te...
Scheme 7: Synthesis of NR+Cl− from NR+OTf− by means of ion exchange with sodium chloride solution.
Scheme 8: Synthesis of acylated NR+OTf− by means of ion exchange with sodium chloride.
Scheme 9: Synthesis of triacetylated derivatives of NAR+ by glycosylation of nicotinic acid esters with ribos...
Scheme 10: Synthesis of NR+OTf− from the triflate salt of ethyl nicotinate-2,3,5-triacetyl-β-D-riboside in met...
Scheme 11: Reaction of 2,3,5-tri-O-acetyl-β-phenyl nicotinate riboside triflate salt with secondary and tertia...
Scheme 12: Synthesis of NMN based on the Zincke reaction of N-(2,4-dinitrophenyl)-3-carbamoylpyridinium chlori...
Scheme 13: Synthesis of NMN based on the Zincke reaction of N-(2,4-dinitrophenyl)-3-carbamoylpyridinium chlori...
Scheme 14: Efficacious protection of 2′,3′-hydroxy groups of NR+X−.
Scheme 15: Protection of the 2′,3′-hydroxy groups of NR+Cl– with a mesitylmethylene acetal group.
Figure 5: Reduction of derivatives of NR+Xˉ into corresponding 1,2-; 1,4-; 1,6-NRH derivatives.
Figure 6: Mechanism of the reduction of the pyridinium core with dithionite as adapted from [67].
Scheme 16: Reduction of triacylated NR+OTf– derivatives by sodium dithionite followed by complete removal of a...
Figure 7: Structural formulas of iridium and rhodium catalysts (a)–(d) for regeneration of NAD(P)H from NAD(P)...
Figure 8: Two approaches to synthesis of 5′-derivatives of NR+.
Scheme 17: Synthesis of NMN starting from NR+ salt.
Scheme 18: Efficient synthesis of NMN by phosphorylation of 2′,3′-O-isopropylidene-NR+ triflate followed by re...
Scheme 19: Synthesis of a bisphosphonate analogue of β-NAD+ based on DCC-induced conjugation of 2′,3′-O-isopro...
Scheme 20: Synthesis of 5′-acyl and 2′,3′,5′-triacyl derivatives of NR+.
Figure 9: Structural formulas of NMN analogues 39–41.
Scheme 21: Synthesis of 5′-phosphorylated derivatives of NR+ using a “reduction–modification–oxidation” approa...
Scheme 22: Synthesis of 5′-phosphorylated derivatives of NR+ using a “reduction–modification–reoxidation” appr...
Figure 10: Structural formulas of 5′-phosphorylated derivatives of NR+.
Scheme 23: Synthesis of 5′-phosphorylated derivatives of NR+ using a direct NR+ phosphorylation approach.
Figure 11: Structural formulas of amino acid NR+ conjugates.
Scheme 24: Synthesis of amino acid NR+ conjugates using NRH and protected amino acid under CDI-coupling condit...
Figure 12: Chemical structures of known isotopically labelled NR+ analogues and derivatives.
Scheme 25: Synthesis of [2′-3H]-NR+ and [2′-3H]-NMN.
Scheme 26: Synthesis of α- and β-anomers of [1′-2H]-NMN.
