ISSN:
1432-1424
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
Summary The synthesis of “amphiphilic” flavins substituted with C18-hydrocarbon sidechains in positions 3, 5, 7, 8 and 10 is described. 3-, 7-, and 10-amphiflavins were obtained by new total syntheses. Furthermore, 3-amphiflavin was obtained by C18-alkylation of natural flavin in the oxidized state, whereas 5-amphi(dihydro)flavin was obtained by alkylation under reducing conditions. In the course of these studies, a novel, selective oxidation reaction was found taking place with the 8-methyl group of natural flavins. In this way lumiflavin and riboflavin derivatives could be converted directly to flavin-8-nor-8-carboxylic acids or the corresponding alkyl esters. The new flavin derivatives lend themselves for incorporation into lipid vesicles, thus yielding the basis for model studies of “anisotropic flavin chemistry” and redox transfer through membranes, as described in the concomitant paper (Schmidt, W., Hemmerich, P. 1981).J. Membrane Biol. 59:129. The new flavins are characterized by means of absorption, fluorescence, and proton nuclear magnetic resonance spectroscopy.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01870416
