Biosynthesis of 5-hydroxy-4-oxo-L-norvaline in Streptomyces akiyoshiensis
White, RL; Smith, KC; Demarco, AC
| HERO ID | 4932902 |
|---|---|
| In Press | No |
| Year | 1994 |
| Title | Biosynthesis of 5-hydroxy-4-oxo-L-norvaline in Streptomyces akiyoshiensis |
| Authors | White, RL; Smith, KC; Demarco, AC |
| Journal | Canadian Journal of Chemistry |
| Volume | 72 |
| Issue | 7 (1994) |
| Page Numbers | 1645-1655 |
| Abstract | The biosynthesis of 5-hydroxy-4-oxo-L-norvaline (HON) in Streptomyces akiyoshiensis has been investigated using super(13)C-labelled substrates. Incorporations of super(13)C label from sodium [1- super(13)C]-, [2- super(13)C]-, and [1,2- super(13)C sub(2)]acetate indicated that HON was formed from a four-carbon compound derived from the citric acid cycle and the methyl carbon of acetate. Feeding experiments using DL-[4- super(13)C]- and DL-[2- super(13)C, super(15)N]aspartate demonstrated that aspartate served as the four-carbon precursor to HON. Both enantiomers of aspartate were metabolized by S. akiyoshiensis, but the D isomer was consumed at a slower rate. The distribution of super(13)C label in the intracellular L-glutamic acid isolated in these feeding experiments is consistent with the operation of the citric acid cycle in S. akiyoshiensis. A biosynthetic hypothesis that involves a condensation reaction between acetyl or malonyl CoA and the beta -carboxyl group of aspartate, and subsequent oxidative decarboxylation, is proposed to account for the incorporation results. An analogous condensation step has been proposed for the biosynthesis of other natural products, including the carbapenem antibiotics. DL-[2- super(13)C, super(15)N]Aspartate was synthesized from [2- super(13)C]diethylmalonate and potassium [ super(15)N]phthalimide via diethyl [2- super(13)C, super(15)N]phthalimidomalonate. |
| Doi | 10.1139/v94-207 |
| Wosid | WOS:A1994NY88400008 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | anabolism; amino acids |