N-Benzylnicotinamide and N-benzyl-1,4-dihydronicotinamide: Useful models for NAD+ and NADH

John M. Moore, Jasmine M. Hall, Wendell L. Dilling, Anton W. Jensen, Philip J. Squattrito, Patrick Giolando, Kristin Kirschbaum

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

3-Aminocarbonyl-1-benzylpyridinium bromide (N-benzylnicotinamide, BNA), C13H13N2O+ Br, (I), and 1-benzyl-1,4-dihydropyridine-3-carboxamide (N-benzyl- 1,4-dihydronicotinamide, rBNA), C13H14N2O, (II), are valuable model compounds used to study the enzymatic cofactors NAD(P)+ and NAD(P)H. BNAwas crystallized successfully and its structure determined for the first time, while a low-temperature high-resolution structure of rBNA was obtained. Together, these structures provide the most detailed view of the reactive portions of NAD(P)+ and NAD(P)H. The amide group in BNA is rotated 8.4 (4) out of the plane of the pyridine ring, while the two rings display a dihedral angle of 70.48 (17). In the rBNA structure, the dihydropyridine ring is essentially planar, indicating significant delocalization of the formal double bonds, and the amide group is coplanar with the ring [dihedral angle = 4.35 (9)]. This rBNA conformation may lower the transition-state energy of an ene reaction between a substrate double bond and the dihydropyridine ring. The transition state would involve one atom of the double bond binding to the carbon ortho to both the ring N atom and the amide substituent of the dihydropyridine ring, while the other end of the double bond accepts an H atom from the methylene group para to the N atom.

Original languageEnglish
Pages (from-to)531-535
Number of pages5
JournalActa Crystallographica Section C: Structural Chemistry
Volume73
Issue number7
DOIs
StatePublished - Jul 2017

Keywords

  • NAD(P)
  • NAD(P)H
  • crystal structure
  • dinucleotide
  • ene reaction
  • enzymatic cofactor
  • nicotinamide
  • pyridinium
  • salt

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