Identification and functional characterization of phenylglycine biosynthetic genes involved in pristinamycin biosynthesis in Streptomyces pristinaespiralis

Journal of Biotechnology

Volumn 155, Issue 1, 2011, Pages 63-67

  Mast, Yvonne J ^a   Wohlleben, Wolfgang ^a   Schinko, Eva ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Antibiotics; Aproteinogenic amino acid; Nonribosomal polypeptide; Phenylglycine; Precursor supply; Streptogramin

Indexed keywords

APROTEINOGENIC AMINO ACID; NONRIBOSOMAL POLYPEPTIDE; PHENYLGLYCINES; PRECURSOR SUPPLY; STREPTOGRAMINS;

AMINO ACIDS; ANTIBIOTICS; BACTERIA; BIOCHEMISTRY; BIOSYNTHESIS;

GENES;

AMINO ACID; ANTIBIOTIC AGENT; BACTERIAL DNA; GENE PRODUCT; PHENYLGLYCINE; PRISTINAMYCIN;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; CHEMICAL STRUCTURE; GENE INSERTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MUTAGENESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES PRISTINAESPIRALIS;

BACTERIAL PROTEINS; BASE SEQUENCE; COMPUTER SIMULATION; GENES, BACTERIAL; GLYCINE; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR SEQUENCE DATA; MUTAGENESIS, INSERTIONAL; PRISTINAMYCIN; STREPTOMYCES;

STREPTOMYCES PRISTINAESPIRALIS;

EID: 79961206960     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2010.12.001     Document Type: Article

References (31)

1. Altschul S.F., Gish W., Miller W., Myers E.W., Lipman D.J. Basic local alignment search tool. J. Mol. Biol. 1990, 215:403-410.
2. Bibb M.J., Findlay P.R., Johnson M.W. The relationship between base composition and codon usage in bacterial genes and its use for the simple and reliable identification of protein-coding sequences. Gene 1984, 30:157-166.
3. Blanc, V., Blanche, F., Crouzet, J., Jacques, N., Lacroix, P., Thibaut, D., Zagorec, M., Debussche, L., de Crécy-Lagard, V., 1994. Polypeptides involved in streptogramin biosynthesis, nucleotide sequences coding for said polypeptides and use thereof. Patent Cooperation Treaty International Publication no. WO 94/08014. Derwent, London, England.
4. Bullock W.O., Fernandez J.M., Short J.M. Xl1-Blue, a high efficiency plasmid transforming recA Escherichia coli strain with beta galactosidase selection. Focus 1987, 5:376-378.
5. Chiu H.T., Hubbard B.K., Shah A.N., Eide J., Fredenburg R.A., Walsh C.T., Khosla C. Molecular cloning and sequence analysis of the complestatin biosynthetic gene cluster. PNAS 2001, 98:8548-8553.
6. Claxton H.B., Akey D.L., Silver M.K., Admiraal S.J., Smith J.L. Structure and functional analysis of RifR, the type II thioesterase from the rifamycin biosynthetic pathway. J. Biol. Chem. 2009, 284:5021-5029.
7. Cocito C.G. Antibiotics of the virginiamycin family, inhibitors which contain synergistic components. Microb. Rev. 1979, 43:145-198.
8. de Crécy-Lagard V., Saurin W., Thibaut D., Gil P., Naudin L., Crouzet J., Blanc Y. Streptogramin B biosynthesis in Streptomyces pristinaespiralis and Streptomyces virginiae: molecular characterization of the last structural peptide synthetase gene. Antimicrob. Agents Chemother. 1997, 41:1904-1909.
9. Eliopoulos G.M. Quinupristin-dalfopristin and linezolid: evidence and opinion. Clin. Infect. Dis. 2003, 36:473-481.
10. Felnagle E.A., Barkei J.J., Park H., Podevels A.M., McMahon M.D., Drott D.W., Thomas M.G. MbtH-like proteins as integral components of bacterial nonribosomal peptide synthetases. Biochemistry 2010, 49:8815-8817.
11. Fiedler H.P. Screening for secondary metabolite products by HPLC and UV-visible absorbance spectral libraries. Nat. Prod. Lett. 1993, 2:99-128.
12. Heathcote M.L., Staunton J., Leadlay P.F. Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units. Chem. Biol. 2001, 8:207-220.
13. Heinzelmann E., Kienzlen G., Kaspar S., Recktenwald J., Wohlleben W., Schwartz D. The phosphinomethylmalate isomerase gene pmi, encoding an aconitase-like enzyme, is involved in the synthesis of phosphinothricin tripeptide in Streptomyces viridochromogenes. Appl. Environ. Microbiol. 2001, 67:3603-3609.
14. Kieser T., Bibb M.J., Buttner M.J., Chater K.F., Hopwood D.A. Practical Streptomyces Genetics 2000, John Innes Foundation, Norwich.
15. Lautru S., Oves-Costales D., Pernodet J.-L., Challis G.L. MbtH-like protein-mediated cross-talk between non-ribosomal peptide antibiotic and siderophore biosynthetic pathways in Streptomyces coelicolor M145. Microbiology 2007, 153:1405-1412.
16. Li L., Bannantine J.P., Zhang Q., Amonsin A., May B.J., Alt D., Banerji N., Kanjilal S., Kapur V. The complete genome sequence of Mycobacterium avium subspecies paratuberculosis. PNAS 2005, 102:12344-12349.
17. Mast Y., Weber T., Gölz M., Ort-Winklbauer R., Gondran A., Wohlleben W., Schinko E. Characterization oft the 'pristinamycin supercluster' of Streptomyces pristinaespiralis. Microb. Biotechnol. 2010, 10.1111/j.1751-7915.2010.00213.x.
18. Müller U., van Assema F., Gunsior M., Orf S., Kremer S., Schipper D., Wagemans A., Townsend C.A., Sonke T., Bovenberg R., Wubbolts M. Metabolic engineering of the E. coli l-phenylalanine pathway for the production of d-phenylglycine (d-Phg). Metab. Eng. 2006, 8:196-208.
19. Pelzer S., Süssmuth R., Heckmann D., Recktenwald J., Huber P., Jung G., Wohlleben W. Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908. Antimicrob. Agents Chemother. 1999, 43:1565-1573.
20. Pfeifer V., Nicholson G.J., Ries J., Recktenwald J., Schefer A.B., Shawky R.M., Schröder J., Wohlleben W., Pelzer S. A polyketide synthase in glycopeptide biosynthesis. J. Biol. Chem. 2001, 276:38370-38377.
21. Pridmore R.D. New and versatile cloning-vectors with kanamycin-resistance marker. Gene 1987, 56:309-312.
22. Quadri L.E.N, Sello J., Keating T.A., Weinreb P.H., Walsh C.T. Identification of a Mycobacterium tuberculosis gene cluster encoding the biosynthetic enzymes for assembly of the virulence-conferring siderophore mycobactin. Chem. Biol. 1998, 5:631-645.
23. Sanger F., Nicklen S., Coulson A.R. DNA sequencing with chain terminating inhibitors. PNAS 1977, 74:5463-5467.
24. Schwarzer D., Mootz H.D., Linne U., Marahiel M.A. Regeneration of misprimed nonribosomal peptide synthetases by type II thioesterases. PNAS 2002, 99:14083-14088.
25. Staden R., McLachlan A.D. Codon preference and its use in identifying protein coding regions in large DNA sequences. Nucleic Acids Res. 1982, 10:141-156.
26. Stegmann E., Rausch C., Stockert S., Burkert D., Wohlleben W. The small MbtH-like protein encoded by an internal gene of the balhimycin biosynthetic gene cluster is not required for glycopeptide production. FEMS Microbiol. Lett. 2006, 262:85-92.
27. Thibaut D., Bisch D., Ratet N., Maton L., Couder M., Debussche L., Blanche F. Purification of peptide synthetases involved in pristinamycin I biosynthesis. J. Bacteriol. 1997, 179:697-704.
28. Tseng C.C., Vaillancourt F.H., Bruner S.D., Walsh C.T. DpgC is a metal- and cofactor-free 3,5-dihydroxyphenylacetyl-CoA 1,2-dioxygenase in the vancomycin biosynthetic pathway. Chem. Biol. 2004, 11:1195-1203.
29. Widboom P.F., Fielding E.N., Liu Y., Bruner S.D. Structural basis for cofactor-independent dioxygenation in vancomycin biosynthesis. Nature 2007, 447:342-345.
30. Wolpert M., Gust B., Kammerer B., Heide L. Effects of deletions of mbtH-like genes on clorobiocin biosynthesis in Streptomyces coelicolor. Microbiology 2007, 153:1413-1423.
31. Zhang W., Heemtra J.R., Walsh C.T., Imker H.J. Activation of the pacidamycin PacL adenylation domain by MbtH-like proteins. Biochemistry 2010, 10.1021/bi101539b.