ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The pyramidal inversion of the N(5)-centre of several reduced flavins was measured by NMR. The inversion barrier was found to be ∼10 kcal/mol in acetone solutions and to be independent of the size of the N(5) substituent. An increase of the inversion barrier of ∼5 kcal/mol was observed in the case where the N(5) substituent could only be in axial position, and an increase of ∼3.5 kcal/mol was observed for an acyl-like N(5) substituent. In aqueous solution the inversion barrier increases by ∼3 kcal/mol. The stereochemistry of reduced flavin and its potential relevance in flavin-dependent biological dehydrogenations is discussed.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19730560209
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