Elaboration of Neosamine Rings in the Biosynthesis of Neomycin and Butirosin

The proteins Neo-11 and Neo-18 encoded in the neomycin gene cluster (neo) of Streptomyces fradiae NCIMB 8233 have been characterized as glucosaminyl-6'-oxidase and 6'-oxoglucosaminyl:L-glutamate aminotransferase, respectively. The joint activity of Neo-11 and Neo-18 is responsible for the...

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Bibliographic Details
Published in:Chembiochem : a European journal of chemical biology 2007-02, Vol.8 (3), p.283-288
Main Authors: Huang, Fanglu, Spiteller, Dieter, Koorbanally, Neil A, Li, Yanyan, Llewellyn, Nicholas M, Spencer, Jonathan B
Format: Article
Language:English
Subjects:
aminoglycosides
Anti-Bacterial Agents - biosynthesis
Bacillus - enzymology
Bacillus - genetics
biosynthesis
butirosin
Butirosin Sulfate - biosynthesis
Carbohydrate Sequence
Cyclization
Glucosamine - analogs & derivatives
Glucosamine - chemistry
Glucosamine - classification
Molecular Sequence Data
Multigene Family
neomycin
Neomycin - biosynthesis
oxidases
Oxidoreductases - chemistry
Oxidoreductases - genetics
Oxidoreductases - metabolism
Streptomyces - enzymology
Streptomyces - genetics
Transaminases - chemistry
Transaminases - genetics
Transaminases - metabolism
transferases
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Summary:The proteins Neo-11 and Neo-18 encoded in the neomycin gene cluster (neo) of Streptomyces fradiae NCIMB 8233 have been characterized as glucosaminyl-6'-oxidase and 6'-oxoglucosaminyl:L-glutamate aminotransferase, respectively. The joint activity of Neo-11 and Neo-18 is responsible for the conversion of paromamine to neamine in the biosynthetic pathway of neomycin through a mechanism of FAD-dependent dehydrogenation followed by a pyridoxal-5'-phosphate-mediated transamination. Neo-18 is also shown to catalyze deamination at C-6''' of neomycin, thus suggesting bifunctional roles of the two enzymes in the formation of both neosamine rings of neomycin. The product of the btrB gene, a homologue of neo-18 in the butirosin biosynthetic gene cluster (btr) in Bacillus circulans, exhibits the same activity as Neo-18; this indicates that there is a similar reaction sequence in both butirosin and neomycin biosynthesis.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.200600371