Identification of phenolyl cobamide from the homoacetogenic bacterium Sporomusa ovata.
Phenolyl cobamide was isolated from cyanide extractions of the anaerobic eubacterium Sporomusa ovata. The proposed corrinoid structure [Co alpha,Co beta-(monocyano,monoaquo)-phenolyl cobamide] has been deduced from 1H NMR, fast-atom-bombardment mass spectroscopy and ultraviolet/visible spectroscopy data. The complete corrinoid resembled p-cresolyl cobamide [Co alpha,Co beta-(monocyano,monoaquo)-p-cresolyl cobamide], which recently has been obtained from cyanide extractions of the same bacterium. The structures and chemical properties of both cobamides with uncoordinated nucleotides differed significantly from those of vitamin B12 [Co alpha-[alpha-(5,6-dimethylbenzimidazolyl)]-Co beta-cyanocobamide]. Sporomusa synthesized coenzymes of phenolyl cobamide and p-cresolyl cobamide in considerable amounts of 400 nmol/g and 1700 nmol/g dry cells, respectively. More than 90% of the complete corrinoid pool of the homoacetogenic bacterium consisted of these two corrinoids, indicating that they are physiologically important coenzymes of the bacterial metabolism.
Stupperich
E
E
Abteilung Angewandte Mikrobiologie, Universität Ulm, Federal Republic of Germany.
Eisinger
H J
HJ
Kräutler
B
B
D001419:Bacteria / Q000032:analysis; D001421:Bacteria, Anaerobic / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D003038:Cobamides / Q000302:isolation & purification*; D005051:Eubacterium / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013053:Spectrophotometry
D003038:Cobamides; C062497:phenolyl cobamide