MICROBIAL PRODUCTION OF VITAMIN B12 ANTIMETABOLITES. IV ISOLATION AND IDENTIFICATION OF 4-KETO-5-AMINO-6-HYDROXYHEXANOIC ACID

4-Keto-5-amino-6-hydroxyhexanoic acid was isolated fromBacillus cereus 102804 fermentations and found to inhibit the growth of Gram-positive and Gram-negative bacteria, when grown in a chem δ-aminolevulinic acid dehydratase. The Ki value of 4-keto-5-amino-6-hydroxyhexanoic acid in an enzyme preparat...

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Bibliographic Details
Published inJournal of antibiotics Vol. 34; no. 5; pp. 483 - 488
Main Authors PERLMAN, KATO L., SCHÖMER, ULRIKE, WILLIAMS, TOM H ., PERLMAN, DAVID
Format Journal Article
LanguageEnglish
Published Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1981
Subjects
Aminocaproates
Antimetabolites - isolation & purification
Bacillus cereus - metabolism
Bacteria - growth & development
Caproates - chemical synthesis
Caproates - isolation & purification
Chemical Phenomena
Chemistry
Fermentation
Kinetics
Porphobilinogen Synthase - antagonists & inhibitors
Vitamin B 12 - metabolism
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Summary:4-Keto-5-amino-6-hydroxyhexanoic acid was isolated fromBacillus cereus 102804 fermentations and found to inhibit the growth of Gram-positive and Gram-negative bacteria, when grown in a chem δ-aminolevulinic acid dehydratase. The Ki value of 4-keto-5-amino-6-hydroxyhexanoic acid in an enzyme preparation ofPropionibacterium shermanii was 0.72 μM. Similar test conditions with 4-keto-5-aminohexanoic acid resulted in a Ki of 12.1 μM. In both cases competitive inhibition was found. The structure of 4-keto-5-amino-6-hydroxyhexanoic acid was determined.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.34.483