NMR.-study of nitrogen inversion and conformation of 1,5-dihydro-isoalloxazines ('Reduced Flavin')

Tauscher, Ludwig; Ghisla, Sandro; Hemmerich, Peter

NMR.-study of nitrogen inversion and conformation of 1,5-dihydro-isoalloxazines ('Reduced Flavin')

Files

NMR.pdf(959.93 KB)

Date

1973

Authors

Tauscher, Ludwig

Ghisla, Sandro

Hemmerich, Peter

Publication type

Journal article

Published in

Helvetica Chimica Acta ; 56 (1973), 2. - pp. 630-644. - ISSN 0018-019X. - eISSN 1522-2675

Abstract

Thc 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.

Subject (DDC)

570 Biosciences, Biology

Cite This

ISO 690

TAUSCHER, Ludwig, Sandro GHISLA, Peter HEMMERICH, 1973. NMR.-study of nitrogen inversion and conformation of 1,5-dihydro-isoalloxazines ('Reduced Flavin'). In: Helvetica Chimica Acta. 56(2), pp. 630-644. ISSN 0018-019X. eISSN 1522-2675. Available under: doi: 10.1002/hlca.19730560209

BibTex

@article{Tauscher1973NMRst-7448,
  year={1973},
  doi={10.1002/hlca.19730560209},
  title={NMR.-study of nitrogen inversion and conformation of 1,5-dihydro-isoalloxazines ('Reduced Flavin')},
  number={2},
  volume={56},
  issn={0018-019X},
  journal={Helvetica Chimica Acta},
  pages={630--644},
  author={Tauscher, Ludwig and Ghisla, Sandro and Hemmerich, Peter}
}

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