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. https://doi.org/10.3762/bjoc.15.36

Cite the Following Article

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. https://doi.org/10.3762/bjoc.15.36

How to Cite

Makarov, M. V.; Migaud, M. E. Beilstein J. Org. Chem. 2019, 15, 401–430. doi:10.3762/bjoc.15.36

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 375.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Du, C.; Dang, M.; Ming, D.; Zhang, Z.; Hu, X.; Ren, L. Structure-guided mining and engineering of nicotinamide riboside kinase for efficient synthesis of nicotinamide mononucleotide. Molecular Catalysis 2024, 559, 114058. doi:10.1016/j.mcat.2024.114058
  • Biţă, A.; Scorei, I. R.; Ciocîlteu, M. V.; Nicolaescu, O. E.; Pîrvu, A. S.; Bejenaru, L. E.; Rău, G.; Bejenaru, C.; Radu, A.; Neamţu, J.; Mogoşanu, G. D.; Benner, S. A. Nicotinamide Riboside, a Promising Vitamin B3 Derivative for Healthy Aging and Longevity: Current Research and Perspectives. Molecules (Basel, Switzerland) 2023, 28, 6078. doi:10.3390/molecules28166078
  • Metcalfe, M.; David, B. T.; Langley, B. C.; Hill, C. E. Elevation of NAD+ by nicotinamide riboside spares spinal cord tissue from injury and promotes locomotor recovery. Experimental neurology 2023, 368, 114479. doi:10.1016/j.expneurol.2023.114479
  • Dotsenko, V. V.; Jassim, N. T.; Temerdashev, A. Z.; Abdul-Hussein, Z. R.; Aksenov, N. A.; Aksenova, I. V. New 6'-Amino-5'-cyano-2-oxo-1,2-dihydro-1'H-spiro[indole-3,4'-pyridine]-3'-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity. Molecules (Basel, Switzerland) 2023, 28, 3161. doi:10.3390/molecules28073161
  • Huang, Z.; Wang, X.; Li, N.; Song, F.; Zhou, J. Systematic engineering of Escherichia coli for efficient production of nicotinamide riboside from nicotinamide and 3-cyanopyridine. Bioresource technology 2023, 377, 128953. doi:10.1016/j.biortech.2023.128953
  • Neuburger, J. E.; Tiedemann, S.; Michalik, D.; von Langermann, J. Rare Earth Element‐Based Recovery Concept for Cofactors Containing Phosphate Groups from Aqueous Solutions. Chemical Engineering & Technology 2023, 46, 766–775. doi:10.1002/ceat.202200393
  • Metcalfe, M.; David, B. T.; Langley, B. C.; Hill, C. E. Elevation of NAD+ by nicotinamide riboside spares spinal cord tissue from injury and promotes locomotor recovery. Cold Spring Harbor Laboratory 2023. doi:10.1101/2023.01.17.524307
  • He, Z.; Yang, X.; Tian, X.; Li, L.; Liu, M. Yeast Cell Surface Engineering of a Nicotinamide Riboside Kinase for the Production of β-Nicotinamide Mononucleotide via Whole-Cell Catalysis. ACS synthetic biology 2022, 11, 3451–3459. doi:10.1021/acssynbio.2c00350
  • Sharma, C.; Donu, D.; Cen, Y. Emerging Role of Nicotinamide Riboside in Health and Diseases. Nutrients 2022, 14, 3889. doi:10.3390/nu14193889
  • Cercillieux, A.; Ciarlo, E.; Canto, C. Balancing NAD+ deficits with nicotinamide riboside: therapeutic possibilities and limitations. Cellular and molecular life sciences : CMLS 2022, 79, 463. doi:10.1007/s00018-022-04499-5
  • Ngivprom, U.; Lasin, P.; Khunnonkwao, P.; Worakaensai, S.; Jantama, K.; Kamkaew, A.; Lai, R.-Y. Synthesis of Nicotinamide Mononucleotide from Xylose via Coupling Engineered Escherichia coli and a Biocatalytic Cascade. Chembiochem : a European journal of chemical biology 2022, 23, e202200071. doi:10.1002/cbic.202200071
  • Qian, X.-L.; Dai, Y.-S.; Li, C.-X.; Pan, J.; Xu, J.-H.; Mu, B. Enzymatic synthesis of high-titer nicotinamide mononucleotide with a new nicotinamide riboside kinase and an efficient ATP regeneration system. Bioresources and bioprocessing 2022, 9, 26. doi:10.1186/s40643-022-00514-6
  • Belen'kii, L. I.; Gazieva, G. A.; Evdokimenkova, Y. B.; Soboleva, N. O. The literature of heterocyclic chemistry, Part XIX, 2019. Advances in Heterocyclic Chemistry; Elsevier, 2022; pp 225–295. doi:10.1016/bs.aihch.2021.09.002
  • Singh, B.; Das, R. S. PCET to bound-superoxide by NADH and NADHX in aqueous-acid media: a kinetic inspection. Journal of Chemical Sciences 2021, 133, 1–9. doi:10.1007/s12039-021-01994-3
  • Zarei, A.; Khazdooz, L.; Enayati, M.; Madarshahian, S.; Wooster, T. J.; Ufheil, G.; Abbaspourrad, A. Dihydronicotinamide riboside: synthesis from nicotinamide riboside chloride, purification and stability studies. RSC advances 2021, 11, 21036–21047. doi:10.1039/d1ra02062e
  • Schabert, G.; Haase, R.; Parris, J.; Pala, L.; Hery-Barranco, A.; Spingler, B.; Spitz, U. New Crystalline Salts of Nicotinamide Riboside as Food Additives. Molecules (Basel, Switzerland) 2021, 26, 2729. doi:10.3390/molecules26092729
  • Makarov, M. V.; Hayat, F.; Graves, B.; Sonavane, M.; Salter, E. A.; Wierzbicki, A.; Gassman, N. R.; Migaud, M. E. Chemical and Biochemical Reactivity of the Reduced Forms of Nicotinamide Riboside. ACS chemical biology 2021, 16, 604–614. doi:10.1021/acschembio.0c00757
  • Black, W. B.; Aspacio, D.; Bever, D.; King, E.; Zhang, L.; Li, H. Metabolic engineering of Escherichia coli for optimized biosynthesis of nicotinamide mononucleotide, a noncanonical redox cofactor. Microbial cell factories 2020, 19, 150. doi:10.1186/s12934-020-01415-z
  • Mehmel, M.; Jovanovic, N.; Spitz, U. Nicotinamide Riboside-The Current State of Research and Therapeutic Uses. Nutrients 2020, 12, 1616. doi:10.3390/nu12061616
  • Black, W. B.; Aspacio, D.; Bever, D.; King, E.; Zhang, L.; Li, H. Metabolic engineering of Escherichia coli for optimized biosynthesis of nicotinamide mononucleotide, a noncanonical redox cofactor. Cold Spring Harbor Laboratory 2020. doi:10.1101/2020.05.11.089011

Patents

  • KREMSKY JONATHAN N; SZCZEPANKIEWICZ BRUCE; KOPPETSCH KARSTEN; HARRIS JOSEPH; PITAK MATEUSZ; BATES MARTIN. Crystalline solids of nicotinic acid mononucleotide and esters thereof and methods of making and use. US 11787830 B2, Oct 17, 2023.
  • MALKANNAGARI RAMANI; GUNDAPUNENI RAGHAVA RAO; BOHAN FRODE. A PROCESS FOR SYNTHESIS OF NICOTINAMIDE RIBOSIDE CHLORIDE (NRCL). WO 2022233923 A1, Nov 10, 2022.
  • NORMINGTON KARL D; SINCLAIR DAVID A; LIVINGSTON DAVID J; MCKEARIN JAMES M; SZCZEPANKIEWICZ BRUCE; KREMSKY JONATHAN N. Nicotinamide mononucleotide derivatives and their uses. US 11464796 B2, Oct 11, 2022.
  • SCHABERT GÜNTER; SPITZ URS; SOYDEMIR AYSEL; ZIMMERMANN IRIS. METHOD OF MAKING NICOTINAMIDE RIBOFURANOSIDE SALTS BY SALT METATHESIS, THE CRYSTALLINE FORM OF ITS TOSYLATE SALT AND THE CO-CRYSTALLIZED FORM OF ITS CHLORIDE:IODIDE SALT. WO 2022157173 A1, July 28, 2022.
  • BAEVSKY MATTHEW; SZCZEPANKIEWICZ BRUCE; LAVERY KAREN; LIVINGSTON DAVID J. Anti-viral compounds and methods of use. US 11279727 B2, March 22, 2022.
  • BAEVSKY MATTHEW; SZCZEPANKIEWICZ BRUCE; LAVERY KAREN; LIVINGSTON DAVID. ANTI-VIRAL COMPOUNDS AND METHODS OF USE. WO 2021257569 A1, Dec 23, 2021.
  • BERMOND GUILLAUME; GARÇON LAURENT. DÉRIVÉS DE NICOTINAMIDE MONONUCLÉOTIDES DANS LE TRAITEMENT ET LA PRÉVENTION DES INFECTIONS BACTÉRIENNES. FR 3108502 A1, Oct 1, 2021.
  • BERMOND GUILLAUME; GARÇON LAURENT. NICOTINAMIDE MONONUCLEOTIDE DERIVATIVES FOR THE TREATMENT OF BACTERIAL INFECTIONS. WO 2021191422 A1, Sept 30, 2021.
  • CANTO ALVAREZ CARLES; CHRISTEN STEFAN; GINER MARIA PILAR; GIROUD-GERBETANT JUDITH; MOCO SOFIA; KWONG CHUNG CHEONG KWET CHOY; CIARLO ELEONORA. COMPOSITIONS AND METHODS CONTAINING REDUCED NICOTINAMIDE RIBOSIDE FOR PREVENTION AND TREATMENT OF VIRAL AND BACTERIAL INFECTIONS. WO 2021180739 A1, Sept 16, 2021.
  • CANTO ALVAREZ CARLES; CHRISTEN STEFAN; GINER MARIA; GIROUD-GERBETANT JUDITH; MOCO SOFIA; KWONG CHUNG CHEONG KWET CHOY. COMPOSITIONS AND METHODS CONTAINING REDUCED NICOTINAMIDE RIBOSIDE FOR PREVENTION AND TREATMENT OF LUNG DISEASES AND CONDITIONS. WO 2021180740 A1, Sept 16, 2021.
  • CANTO ALVAREZ CARLES; CHRISTEN STEFAN; GINER MARIA PILAR; GIROUD-GERBETANT JUDITH; MOCO SOFIA; GUT PHILIPP; JOFFRAUD MAGALI; RICHARD JOY. COMPOSITIONS AND METHODS CONTAINING REDUCED NICOTINAMIDE RIBOSIDE FOR PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES AND CONDITIONS. WO 2021180731 A1, Sept 16, 2021.
  • CANTO ALVAREZ CARLES; CHRISTEN STEFAN; GINER MARIA PILAR; GIROUD-GERBETANT JUDITH; MOCO SOFIA; BARTOVA SIMONA. REDUCED NICOTINAMIDERIBOSIDES FOR TREATING OR PREVENTING KIDNEY DISEASE. WO 2020245187 A1, Dec 10, 2020.
  • CANTO ALVAREZ CARLES; CHRISTEN STEFAN; GINER MARIA PILAR; GIROUD-GERBETANT JUDITH; MOCO SOFIA. REDUCED NICOTINAMIDERIBOSIDES FOR TREATING/PREVENTING SKELETAL MUSCLE DISEASE. WO 2020245191 A1, Dec 10, 2020.
  • CANTO ALVAREZ CARLES; CHRISTEN STEFAN; GINER MARIA PILAR; GIROUD-GERBETANT JUDITH; MOCO SOFIA. REDUCED NICOTINAMIDERIBOSIDES FOR THE TREATMENT/PREVENTION OF LIVER DISEASE. WO 2020245190 A1, Dec 10, 2020.
Other Beilstein-Institut Open Science Activities