Investigations of Valanimycin Biosynthesis: Elucidation of the Role of Seryl-tRNA
The antibiotic valanimycin is a naturally occurring azoxy compound produced by Streptomyces viridifaciens MG456-hF10. Precursor incorporation experiments showed that valanimycin is derived from L-valine and L-serine via the intermediacy of isobutylamine and isobutylhydroxylamine. Enzymatic and genet...
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| Veröffentlicht in: | Proceedings of the National Academy of Sciences - PNAS 2008-05, Vol.105 (18), p.6543-6547 |
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| creator | Garg, Ram P. Qian, Xuelei L. Alemany, Lawrence B. Moran, Sean Parry, Ronald J. |
| description | The antibiotic valanimycin is a naturally occurring azoxy compound produced by Streptomyces viridifaciens MG456-hF10. Precursor incorporation experiments showed that valanimycin is derived from L-valine and L-serine via the intermediacy of isobutylamine and isobutylhydroxylamine. Enzymatic and genetic investigations led to the cloning and sequencing of the valanimycin biosynthetic gene cluster, which was found to contain 14 genes. A novel feature of the valanimycin biosynthetic gene cluster is the presence of a gene (vlmL) that encodes a class II seryl-tRNA synthetase. Previous studies suggested that the role of this enzyme is to provide seryl-tRNA for the valanimycin biosynthetic pathway. Here, we report the results of investigations to elucidate the role of seryl-tRNA in valanimycin biosynthesis. A combination of enzymatic and chemical studies has revealed that the VlmA protein encoded by the valanimycin biosynthetic gene cluster catalyzes the transfer of the seryl residue from seryl-tRNA to the hydroxyl group of isobutylhydroxylamine to produce the ester O-seryl-isobutylhydroxylamine. These findings provide an example of the involvement of an aminoacyl-tRNA in an antibiotic biosynthetic pathway. |
| doi_str_mv | 10.1073/pnas.0708957105 |
| format | Article |
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Precursor incorporation experiments showed that valanimycin is derived from L-valine and L-serine via the intermediacy of isobutylamine and isobutylhydroxylamine. Enzymatic and genetic investigations led to the cloning and sequencing of the valanimycin biosynthetic gene cluster, which was found to contain 14 genes. A novel feature of the valanimycin biosynthetic gene cluster is the presence of a gene (vlmL) that encodes a class II seryl-tRNA synthetase. Previous studies suggested that the role of this enzyme is to provide seryl-tRNA for the valanimycin biosynthetic pathway. Here, we report the results of investigations to elucidate the role of seryl-tRNA in valanimycin biosynthesis. A combination of enzymatic and chemical studies has revealed that the VlmA protein encoded by the valanimycin biosynthetic gene cluster catalyzes the transfer of the seryl residue from seryl-tRNA to the hydroxyl group of isobutylhydroxylamine to produce the ester O-seryl-isobutylhydroxylamine. 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| subjects | Amides Antibiotics Azo Compounds - analysis Azo Compounds - chemistry Azo Compounds - metabolism Bacteria Bacteriology Biological Sciences Biosynthesis Catalysis Chemical equilibrium Chromatography, Thin Layer Enzymes Esters Genes Models, Chemical Multigene family Mutation - genetics Physical Sciences Proteins Ribonucleic acid RNA RNA, Transfer, Amino Acyl - metabolism Streptomyces Streptomyces - metabolism Transfer RNA |
| title | Investigations of Valanimycin Biosynthesis: Elucidation of the Role of Seryl-tRNA |
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