Document Detail

Studies on the biosynthesis of corrinoids and porphyrinoids. I. The labeling of oxygen of vitamin B12.
MedLine Citation:
PMID:  2630086     Owner:  NLM     Status:  MEDLINE    
Recently the amide-oxygen has been suggested to participate in the formation of the corrin ring of vitamin B12. To confirm this hypothesis, 17O-labeled aminolevulinic acid (ALA) was prepared and administered to Propionibacterium shermanii. The isolated vitamin B12 showed only broad 17O signals in the oxygen-17 nuclear magnetic resonance (17O-NMR) spectrum. However, distinct isotope-shifted peaks were observed in the 13C-NMR spectrum of vitamin B12 isolated after incorporation of [1-13C:1,4-18O2]ALA. Of these shifted peaks, one peak (C27) showed very low intensity. This indicates that dilution of 18O occurred at the acetyl chain of the A ring of vitamin B12. This result supports the assumption that the lactone formation of the A ring promotes the ring contraction, as proposed by Eschenmoser.
K Kurumaya; T Okazaki; M Kajiwara
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  37     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  1989 May 
Date Detail:
Created Date:  1990-05-02     Completed Date:  1990-05-02     Revised Date:  2004-01-20    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  1151-4     Citation Subset:  IM    
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MeSH Terms
Oxygen Isotopes
Porphyrins / biosynthesis*
Propionibacterium / metabolism
Vitamin B 12 / biosynthesis*
Reg. No./Substance:
0/Corrinoids; 0/Oxygen Isotopes; 0/Porphyrins; 68-19-9/Vitamin B 12

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