Biosynthetic origin of [R-(Z)]-4-amino-3-chloro-2-pentenedioic acid in Streptomyces viridogenes

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 12, 2006, Pages 3046-3049

  Hutchinson, Robin I ^a   Grant, Russell J ^a   Murphy, Cormac D ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Amino acid; Biosynthesis; Halogenase; Streptomyces

Indexed keywords

HALOGENASE; PENTENEDIOIC ACID (ACPA); STREPTOMYCES;

AMINO ACIDS; BIOSYNTHESIS; CHLORINATION; ENZYMES;

GENETIC ENGINEERING;

4 AMINO 3 CHLORO 2 PENTENEDIOIC ACID; 4-AMINO-3-CHLORO-2-PENTENEDIOIC ACID; GLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; MASS SPECTROMETRY; METABOLISM; STEREOISOMERISM; STREPTOMYCES;

GLUTAMATES; SPECTROMETRY, MASS, SECONDARY ION; STEREOISOMERISM; STREPTOMYCES;

STREPTOMYCES; STREPTOMYCES VIRIDOGENES;

EID: 33845900243     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.60372     Document Type: Article

References (11)

1. Gribble, G. W., Natural organohalogens: a new frontier for medicinal agents. J. Chem. Ed., 81, 1441-1449 (2004).
2. Keller, S., Wage, T., Hohaus, K., Hölzer, M., Eichhorn, E., and van Pée, K. H., Purification and partial characterisation of tryptophan 7-halogenase (PrnA) from Pseudomonas fluorescens. Angew. Chem. Int. Ed. Engl., 39, 2300-2302 (2000).
3. 2-dependent enzyme. Proc. Natl. Acad. Sci. USA, 102, 10111-10116 (2005).
4. Murphy, C. D., Recent developments in enzymatic chlorination. Nat. Prod. Rep., 23, 147-152 (2006).
5. Chaiet, L., Arison, B. H., Monaghan, R. L., Springer, J. P., Smith, J. L., and Zimmerman, S. B., [R-(Z)]-4-amino-3-chloro-2-pentenedioic acid, a new antibiotic. Fermentation, isolation and characterisation. J. Antibiotics, 37, 207-210 (1984).
6. Yasuda, N., and Sakane, K., Revised structure and the chemical transformations of FR900148. J. Antibiotics, 44, 801-802 (1991).
7. 2O, 500 MHz): δ/ppm 6.8 (s, 1H), 5.1 (s, 1H) (lit. 6.8 (s, 1H), 5.2 (s, 1H)). GC-EIMS data for pertrimethylsilyl derivative of 1: m/z = 73 (100), 278 (79), 280 (33), 147 (25), 126 (18), 116 (12), 380 (2), 395 (1).
8. Blasiak, L. C., Vaillancourt, F. H., Walsh, C. T., and Drennan, C. T., Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis. Nature, 440, 368-371 (2006).
9. Nowak-Thompson, B., Chaney, N., Wing, J. S., Gould, S. J., and Loper, J. E., Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J. Bacteriol., 181, 2166-2174 (1999).
10. 2-dependent halogenase PltA during pyoluteorin biosynthesis. Proc. Natl. Acad. Sci. USA, 102, 13843-13848 (2005).
11. Piraee, M., and Vining, L. C., Use of degenerate primers and touchdown PCR to amplify a halogenase gene fragment from Streptomyces venezuelae ISP5230. J. Ind. Microbiol., 29, 1-5 (2002).