Darstellung des Coenzymmetaboliten 1,6‐Dihydro‐6‐oxo‐1‐(β‐D‐ribofuranosyl)‐3‐pyridincarbonsäureamid

Frister, H.; Kemper, K.; Boos, Karl-Siegfried; Schlimme, E.

doi:10.1002/jlac.198519850310

Cited by 11 publications

(3 citation statements)

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“…The N -methylated 6-pyridone were easily generated from their respective chloronicotinic acid precursors as were the ribosylated 6-pyridone according to published syntheses [ 6 , 29 , 30 , 31 , 32 ]. However, N -Me-2PY, 2PYR, N -Me-4PY, and 4PYR converted readily to the methylated ester instead of the amide under aqueous methanolic conditions.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of ribosylated forms of 2PY, 4PY, and 6PY (2PYR, 4PYR, and 6PYR, respectively) is based on Vorbrüggen glycosylation reaction [ 31 , 32 ]. Following silylation of the nucleobase using either HMDS (2-PY and 4-PY) or BSTFA (6-PY), the silylated pyridones were mixed with beta- d -riboside tetraacetate in the presence of a Lewis acid.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (DMSO, d 6 ), δ, ppm: 11.92 (s, 1H, NH), 8.00 (s, 1H, H2), 7.85 (d, J = 9.6 Hz, 1H, H4), 7.72 (s, 1H, NH), 7.18 (s, 1H, NH), 6.32 (d, J = 9.56 Hz, 1H, H5). HRMS calcd for C 12 H 16 NO 7 [M + H] + 139.0508 found 139.0499 [ 31 ].…”

Section: Methodsmentioning

confidence: 99%

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The Biochemical Pathways of Nicotinamide-Derived Pyridones

Hayat

Sonavane

Makarov

et al. 2021

IJMS

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As catabolites of nicotinamide possess physiological relevance, pyridones are often included in metabolomics measurements and associated with pathological outcomes in acute kidney injury (AKI). Pyridones are oxidation products of nicotinamide, its methylated form, and its ribosylated form. While they are viewed as markers of over-oxidation, they are often wrongly reported or mislabeled. To address this, we provide a comprehensive characterization of these catabolites of vitamin B3, justify their nomenclature, and differentiate between the biochemical pathways that lead to their generation. Furthermore, we identify an enzymatic and a chemical process that accounts for the formation of the ribosylated form of these pyridones, known to be cytotoxic. Finally, we demonstrate that the ribosylated form of one of the pyridones, the 4-pyridone-3-carboxamide riboside (4PYR), causes HepG3 cells to die by autophagy; a process that occurs at concentrations that are comparable to physiological concentrations of this species in the plasma in AKI patients.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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The Biochemical Pathways of Nicotinamide-Derived Pyridones

Hayat

Sonavane

Makarov

et al. 2021

IJMS

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Synthesis Of Nucleosides

Vorbrüggen¹,

1999

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This chapter deals with the synthesis of nucleosides (e.g., the formation of N ‐glycosides of sugars such as D ‐ribose or 2‐deoxy‐D‐ribose with heterocyclic nitrogen bases). The methods of nucleoside synthesis have been treated in a number of reviews and monographs. It is now generally accepted that nucleosides were among the first organic compounds formed at the start of evolution in the early history of our planet earth. To support this point, guanine and adenine were heated with D ‐ribose in seawater, which contains the Lewis acid magnesium chloride as catalyst. One thus obtained the nucleosides guanosine and adenosine together with comparable yields of unnatural α‐nucleosides. The latter were gradually photoanomerized to the thermodynamically more stable compounds in overall yields of 5–6%. The furanose form of ribose reacts faster than the pyranose form. Corresponding syntheses of the pyrimidine nucleosides uridine and cytidine from uracil , cytosine and ribose are more problematic and remain an enigma. The recent conversion of glycolaldehyde‐ O ‐phosphate and formaldehyde to ribose‐2,4‐di‐ O ‐phosphate might give new insights into the prebiotic syntheses of uridine and cytidine. The evidence and hypotheses for these prebiotic conversions and the evolution of RNA, as well as the implications of an “RNA World,” have been reviewed. These RNA nucleosides are reduced in vivo as 5′‐ O ‐diphosphates by ribonucleotide reductases to the corresponding 2′‐deoxynucleosides—the building blocks of DNA such as 2′‐deoxyguanosine. The thermodynamically controlled synthesis of these four building blocks of RNA has implications for the design of efficient, high yielding, new methods for the synthesis of the naturally occurring nucleosides, nucleoside antibiotics, and modified nucleosides that may serve as antimetabolites to fight viral and parasitic diseases and cancer. The nucleoside rings in this chapter are depicted arbitrarily in the anti conformation, as occurs predominantly in the crystal and solution (based primarily on NOE‐ 1 H‐ and 13 C‐NMR measurements) forms of pyrimidine nucleosides. Only a few nucleosides, such as 6‐methyluridine, occur with the heterocyclic ring predominantly in the syn conformation. The synthesis of C ‐nucleosides has been reviewed previously and is not covered in this review.

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