Biosynthesis of chloramphenicol in Streptomyces sp. 3022a. Identification of p-amino-L-phenylalanine as a product from the action of arylamine synthetase on chorismic acid - PubMed

• PMID: 4210
• DOI: 10.1139/m76-032

Biosynthesis of chloramphenicol in Streptomyces sp. 3022a. Identification of p-amino-L-phenylalanine as a product from the action of arylamine synthetase on chorismic acid

A Jones et al. Can J Microbiol. 1976 Feb.

Abstract

Products obtained from the action of arylamine synthetase on [G-14C]chorismic acid were fractionated by gel filtration and ion exchange column chromatography to yield a partially purified radioactive component with an arylamine function. From its ultraviolet absorption spectrum and thin-layer chromatographic behaviour the product was considered to be p-aminophenylalanine and the identification was confirmed by co-crystallization with an authentic specimen. Specific deamination of the product with L-amino-acid oxidase indicated that it was the L-epimer. These results strengthen previous evidence that arylamine synthetase is at a branch point in the shikimic acid pathway, specifically diverting intermediates to the synthesis of chloramphenicol.

Similar articles

• Biosynthesis of chloramphenicol in Streptomyces species 3022a: the nature of the arylamine synthetase system.

  Francis MM, Westlake DW. Francis MM, et al. Can J Microbiol. 1979 Dec;25(12):1408-15. doi: 10.1139/m79-220. Can J Microbiol. 1979. PMID: 583399

• Biosynthesis of chloramphenicol in Streptomyces species 3022a. Isotope incorporation experiments with (G-14C) chorismic, (G-14C) prephenic, and (G-14C, 6-3H) shikimic acids.

  Emes A, Floss HG, Lowe DA, Westlake DW, Vining LC. Emes A, et al. Can J Microbiol. 1974 Mar;20(3):347-52. doi: 10.1139/m74-053. Can J Microbiol. 1974. PMID: 4822053 No abstract available.

• Biosynthesis of chloramphenicol in Streptomyces sp. 3022a. Properties of an aminotransferase accepting p-aminophenylalanine as a substrate.

  Jones A, Francis MM, Vining LC. Jones A, et al. Can J Microbiol. 1978 Mar;24(3):238-44. doi: 10.1139/m78-042. Can J Microbiol. 1978. PMID: 647477

• Regulation of chorismate-derived antibiotic production.

  Malik VS. Malik VS. Adv Appl Microbiol. 1979;25:75-93. doi: 10.1016/s0065-2164(08)70147-3. Adv Appl Microbiol. 1979. PMID: 121030 Review. No abstract available.

• From scratch to value: engineering Escherichia coli wild type cells to the production of L-phenylalanine and other fine chemicals derived from chorismate.

  Sprenger GA. Sprenger GA. Appl Microbiol Biotechnol. 2007 Jun;75(4):739-49. doi: 10.1007/s00253-007-0931-y. Epub 2007 Apr 14. Appl Microbiol Biotechnol. 2007. PMID: 17435995 Review.

Cited by

• Characterization and regulation of anthranilate synthetase from a chloramphenicol-producing streptomycete.

  Francis MM, Vining LC, Westlake DW. Francis MM, et al. J Bacteriol. 1978 Apr;134(1):10-6. doi: 10.1128/jb.134.1.10-16.1978. J Bacteriol. 1978. PMID: 306386 Free PMC article.

• Control of antibiotic biosynthesis.

  Martin JF, Demain AL. Martin JF, et al. Microbiol Rev. 1980 Jun;44(2):230-51. doi: 10.1128/mr.44.2.230-251.1980. Microbiol Rev. 1980. PMID: 6991900 Free PMC article. Review. No abstract available.

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • Atypon