Generation of new landomycins by combinatorial biosynthetic manipulation of the LndGT4 gene of the landomycin E cluster in S. globisporus

Chemistry and Biology

Volumn 11, Issue 4, 2004, Pages 547-555

  Ostash, Bohdan ^a   Rix, Uwe ^b   Rix, Lily L Remsing ^b   Liu, Tao ^b   Lombo, Felipe ^c   Luzhetskyy, Andriy ^a   Gromyko, Oleksandr ^a   Wang, Chenchen ^b   Braña, Alfredo F ^c   Méndez, Carmen ^c   Salas, José A ^c   Fedorenko, Victor ^a   Rohr, Jürgen ^b  

^a IVAN FRANKO NATIONAL UNIVERSITY OF LVIV   (Ukraine)

^b University of Kentucky   (United States)

^c DEPARTAMENTO DE BIOQUÍMICA Y BIOLOGÍA MOLECULAR   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; ANTINEOPLASTIC AGENT; GLYCOSYLTRANSFERASE; LANDOMYCIN D; LANDOMYCIN E; LANDOMYCIN F; LANDOMYCIN G; LANDOMYCIN H; MIXED FUNCTION OXIDASE; OXIDOREDUCTASE;

ARTICLE; BIOSYNTHESIS; CELL DIVISION; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; GENETICS; HUMAN; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY; MUTATION; NUCLEOTIDE SEQUENCE; STREPTOMYCES; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

AMINOGLYCOSIDES; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL LINE, TUMOR; GLYCOSYLTRANSFERASES; HUMANS; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; MUTATION; OXIDOREDUCTASES; STREPTOMYCES; STRUCTURE-ACTIVITY RELATIONSHIP;

STREPTOMYCES; STREPTOMYCES GLOBISPORUS;

EID: 1942541277     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.03.011     Document Type: Article

References (33)

1. Krohn K., Rohr J. Angucyclines. Total syntheses, new structures and biosynthetic studies of an emerging new class of antibiotics Top. Curr. Chem. 188:1997;127-195.
2. Rohr J., Wohlert S.-E., Oelkers C., Kirsching A., Ries M. Biosynthetic short activation of the 2,3,6-trideoxysugar L-rhodinose. Chem. Commun. 7:1997;973-974.
3. Westrich L., Domann S., Faust B., Bedford D., Hopwood D.A., Bechthold A. Cloning and characterization of a gene cluster from Streptomyces cyanogenus S136 probably involved in landomycin A biosynthesis. FEMS Microbiol. Lett. 170:1999;381-387.
4. Fedorenko V., Basiliya L.I., Pankevych K.O., Dubitska L.P., Ostash B.O., Luzhetskyy A.M., Gromyko O.M., Krügel H. Genetic control of antitumor antibiotics-polyketides biosynthesis by actinomycetes. Bull. Inst. Agr. Microbiol. (Ukr.). 8:2000;27-31.
5. Luzhetskyy A.M., Ostash B.O., Fedorenko V.O. Intergeneric conjugation Escherichia coli - Streptomyces globisporus 1912 with using of integrative plasmid pSET152 and its derivatives. Russ. J. Genet. 37:2001;1123-1129.
6. Luzhetskyy A., Fedoryshyn M., Hoffmeister D., Bechthold A., Fedorenko V.A. Gene cloning system for Streptomyces cyanogenus S136. Visn. Lviv Univ. Ser. Biol. 29:2002;62-68.
7. Rix U., Fischer C., Remsing L.L., Rohr J. Modification of post-PKS tailoring steps through combinatorial biosynthesis. Nat. Prod. Rep. 19:2002;542-580.
8. Trefzer A., Hoffmeister D., Künzel E., Stockert S., Weitnauer G., Westrich L., Rix U., Fuchser J., Bindseil K.U., Rohr J.et al. Function of glycosyltransferase genes involved in urdamycin A biosynthesis. Chem. Biol. 7:2000;133-142.
9. Raty K., Hautala A., Torkkell S., Kantola J., Mantsala P., Hakala J., Ylihonko K. Characterization of mutations in aclacinomycin A-non-producing Streptomyces galilaeus strains with altered glycosylation patterns. Microbiol. 148:2002;3375-3384.
10. Hoffmeister D., Ichinose K., Bechthold A. Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity. Chem. Biol. 8:2001;557-567.
11. Trefzer A., Pelzer S., Schimana J., Stockert S., Bihlmaier C., Fiedler H.P., Welzel K., Vente A., Bechthold A. Biosynthetic gene cluster of simocyclinone, a natural multihybrid antibiotic. Antimicrob. Agents Chemother. 46:2002;1174-1182.
12. Brünker P., Sterner O., Bailey J.E., Minas W. Heterologous expression of the naphthocyclinone hydroxylase gene from Streptomyces arenae for production of novel hybrid polyketides. Antonie Van Leeuwenhoek. 79:2001;235-245.
13. Sciara G., Kendrew S.G., Miele A.E., Marsh N.G., Federici L., Malatesta F., Schimperna G., Savino C., Vallone B. The structure of ActVA-Orf6, a novel type of monooxygenase involved in actinorhodin biosynthesis. EMBO J. 22:2003;205-215.
14. Rebets Y., Ostash B., Luzhetskyy A., Hoffmeister D., Braña A., Mendez C., Salas J.A., Bechthold A., Fedorenko V. Production of landomycins in strains Streptomyces globisporus 1912 and S. cyanogenus S136 is regulated by genes encoding putative transcriptional activators. FEMS Microbiol. Lett. 222:2003;149-153.
15. Ostash B., Rebets Yu., Yuskevich V., Luzhetskyy A., Tkachenko V., Fedorenko V. Targeted disruption of Streptomyces globisporus 1912 lndF and lndL cyclase genes involved in antitumor landomycin E biosynthesis. Folia Microbiol. (Praha). 48:2003;484-488.
16. Trefzer A., Fischer C., Stockert S., Westrich L., Künzel E., Girreser U., Rohr J., Bechthold A. Elucidation of the function of two glycosyltransferase genes (lanGT1 and lanGT4) involved in landomycin biosynthesis and generation of new oligosaccharide antibiotics. Chem. Biol. 8:2001;1239-1252.
17. Trefzer A., Blanco G., Remsing L., Künzel E., Rix U., Lipata F., Braña A.F., Méndez C., Rohr J., Bechthold A.et al. Rationally designed glycosylated premithramycins. Hybrid aromatic polyketides using genes from three different biosynthetic pathways J. Am. Chem. Soc. 124:2002;6056-6062.
18. Wang L., McVey J., Vining L.C. Cloning and functional analysis of a phosphopantetheinyl transferase superfamily gene associated with jadomycin biosynthesis in Streptomyces venezuelae ISP5230. Microbiol. 147:2001;1535-1545.
19. Kirsching A., Bechthold A., Rohr J. Chemical and biochemical aspects of deoxysugars and deoxysugar oligosaccharides. Top. Curr. Chem. 188:1997;1-84.
20. Filippini S., Solinas M.M., Breme U., Schluter M.B., Gabellini D., Biamonti G., Colombo A.L., Garofano L. Streptomyces peucetius daunorubicin gene, dnrF. Sequence and heterologous expression Microbiol. 141:1995;1007-1016.
21. Méndez C., Salas J.A. Altering the glycosylation pattern of bioactive compounds. Trends Biotechnol. 19:2001;449-456.
22. Flett F., Mersinias V., Smith C.P. High efficiency intergeneric conjugal transfer of plasmid DNA from Escherichia coli to methyl-DNA-restricting streptomycetes. FEMS Microbiol. Lett. 155:1997;223-229.
23. Blondelet-Rouault M.-H., Weiser Y., Lebrihi A., Branny P., Pernodet J.L. Antibiotic resistance gene cassettes derived from the Ω interposon for use in Escherichia coli and Streptomyces. Gene. 190:1997;315-317.
24. Bierman M., Logan R., O'Brien K., Seno E.T., Rao R.N., Schoner B.E. Plasmid cloning vectors for the conjugal transfer of DNA from E. coli to Streptomyces spp. Gene. 116:1992;43-49.
25. Sambrook J., Russel D.W. Molecular Cloning. A Laboratory Manual Third Edition:2001;Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
26. Kieser T., Bibb M.J., Buttner M.J., Chater K.F., Hopwood D.A. Practical Streptomyces Genetics. 2000;The John Innes Foundation, Norwich, United Kingdom.
27. Sanger F., Nicklen S., Coulson A.R. DNA sequencing with chain terminating inhibitors. Proc. Natl. Acad. Sci. USA. 74:1977;5463-5467.
28. Devereux J., Haeberli P., Smithies O. A comprehensive set of sequence analysis programs for the VAX. Nucleic Acids Res. 12:1984;387-395.
29. Altschul S.F., Madden T.L., Schäffer A.A., Zhang J., Zhang Z., Miller W., Lipman D.J. Gapped BLAST and PSI-BLAST. a new generation of protein database search programs Nucleic Acids Res. 25:1997;3389-3402.
30. Henkel T., Rohr J., Beale J., Schwenen L. Landomycins, new angucycline antibiotics from Streptomyces sp. Structural studies on landomycins A-D. J. Antibiot. (Tokyo). 43:1990;492-503.
31. Weber S., Zolke C., Rohr J., Beale J.M. Investigations of the biosynthesis and structural revision of landomycin A. J. Org. Chem. 59:1994;4211-4214.
32. Fernandez-Lozano M.J., Remsing L.L., Quiros L.M., Braña A.F., Fernandez E., Sanchez C., Méndez C., Rohr J., Salas J.A. Characterization of two polyketide methyltransferases involved in the biosynthesis of the antitumor drug mithramycin by Streptomyces argillaceus. J. Biol. Chem. 275:2000;3065-3074.
33. Rodriguez L., Aguirrezabalaga I., Allende N., Braña A.F., Méndez C., Salas J.A. Engineering deoxysugar biosynthetic pathways from antibiotic-producing microorganisms. A tool to produce novel glycosylated bioactive compounds. Chem. Biol. 9:2002;721-729.