An N1-hydrogen bonding model for flavin coenzyme.

Guo F, Chang BH, Rizzo CJ
Bioorg Med Chem Lett. 2002 12 (2): 151-4

PMID: 11755342 · DOI:10.1016/s0960-894x(01)00712-0

A model flavin possessing a specific hydrogen bond to the N1-position has been synthesized. The redox potential has been measured in aqueous buffer and found to be shifted +21 mV as compared to a similar flavin lacking this hydrogen bond. The reaction of the N1-hydrogen-bonding model with sulfite and 1-benzyl-dihydronicotinamide were examined and compared with the non-hydrogen-bonded flavin. The N1-hydrogen bond did not accelerate the rate of sulfite ion or hydride addition to N5, however the N5-sulfite complex was stabilized by nearly 4-fold over a non-hydrogen-bonding model. The model flavins were also studied computationally.

MeSH Terms (4)

Coenzymes Flavins Hydrogen Bonding Models, Molecular

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