Characterization of a chalcosyltransferase (gerGTII) in dihydrochalcomycin biosynthesis

Molecules and Cells

Volumn 26, Issue 3, 2008, Pages 278-284

  Pageni, Binod Babu ^a   Oh, Tae Jin ^a   Thuy, Ta Thi Thu ^a   Sohng, Jae Kyung ^a  

^a SunMoon University   (South Korea)

Author keywords

Dihydrochalcomycin; Gene disruption; Glycosyltransferase; Macrolide; Streptomyces

Indexed keywords

20 O MYCINOSYL DIHYDROCHALCONOLIDE; ANTIBIOTIC AGENT; CHALCOSYLTRANSFERASE; DIHYDROCHALCOMYCIN; GLUCOSYLTRANSFERASE; MACROLIDE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; CHALCOMYCIN; TRANSFERASE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONSENSUS SEQUENCE; CONTROLLED STUDY; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; GENE CLUSTER; GENE DELETION; GENE IDENTIFICATION; GENOME ANALYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PROTEIN FUNCTION; PROTEIN MOTIF; STREPTOMYCES; AMINO ACID SEQUENCE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GENETIC COMPLEMENTATION; GENETICS; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY; SEQUENCE ALIGNMENT;

STREPTOMYCES; STREPTOMYCES SP.; STREPTOMYCES SP. KCTC 0041BP;

AMINO ACID SEQUENCE; BACTERIAL PROTEINS; GENETIC COMPLEMENTATION TEST; MACROLIDES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MULTIGENE FAMILY; SEQUENCE ALIGNMENT; STREPTOMYCES; TRANSFERASES;

EID: 55249119134     PISSN: 10168478     EISSN: None     Source Type: Journal    
DOI: 10.1016/s1016-8478(23)13996-3     Document Type: Article

References (29)

1. Aguirrezabalaga, I., Olano, C., Allende, N., Rodriguez, L., Braña, A.F., Méndez, C., and Salas, J.A. (2000). Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus. Antimicrob. Agents Chemother. 44, 1266-1275.
2. Arakawa, K., Kodama, K., Tatsuno, S., Ide, S., and Kinashi, H. (2006). Analysis of the loading and hydroxylation steps in lankamycin biosynthesis in Streptomyces rochei. Antimicrob. Agents Chemother. 50, 1946-1952.
3. Asolkar, R.N., Maskey, R.P., Helmke, E., and Laatsh, H. (2002). Chalcomycin B, anew macrolide antibiotic from the marine isolate Streptomyces sp. B7064. J. Antibiot. 55, 893-898.
4. Basnet, D.B., Oh, T.J., Vu, T.T., Sthapit, B., Liou, K., Lee, H.C., Yoo, J.C., and Sohng, J.K. (2006). Angucyclines Sch 47554 and Sch 47555 from Streptomyces sp. SCC-2136: cloning, sequencing, and characterization. Mol. Cells 22, 154-162.
5. Bierman, M., Logan, R., O'Brien, K., Seno, E.T., Rao, R.N., and Schoner, B. E. (1992). Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116, 43-49.
6. Denis, F., and Brzezinski, R. (1991). An improved aminoglycoside resistance gene cassette for use in gram-negative bacteria and Streptomyces. FEMS Microbiol. Lett. 65, 261-264.
7. Dürr, C., Hoffmeister, D., Wohlert, S.E., Ichinose, K., Weber, M., Von Mulert, U., Thorson, J.S., and Bechthold, A. (2004). The glycosyltransferase UrdGT2 catalyzes both C- and O-glycosidic sugar transfers. Angew. Chem. Int. Ed. Engl. 43, 2962-2965.
8. Fouces, R., Mellado, E., Diez, B., and Barredo, J.L. (1999). The tylosin biosynthetic cluster from Streptomyces fradiae: genetic organization of the left region. Microbiology 145, 855-868.
9. Goo, Y.M., Lee, Y.Y., and Kim, B.T. (1997). A new 16-membered chalcomycin type macrolide antibiotic, 250-144C. J. Antibiot. 50, 85-88.
10. Jaishy, B.P., Lim, S.K., Yoo, I.D., Yoo, J.C., Sohng, J.K., and Nam, D.H. (2006). Cloning and characterization of a gene cluster for the production of polyketide macrolide dihydrochalcomycin in Streptomyces sp. KCTC0041BP. J. Microbiol. Biotechnol. 16, 764-770.
11. Kieser, T., Bibb, M.J., Buttner, M.J., Chater, K.F., and Hopwood, D.A. (2000). Practical Streptomyces Genetics. The John Innes Centre Foundation, Norwich.
12. Kim, S.D., Ryoo, I.J., Kim, C.J., Kim, W.G., Kim, J.P., Kong, J.Y., Koshino, H., Uramoto, M., and Yoo, I.D. (1996). GERI-155 a new macrolide antibiotic related to chalcomycin. J. Antibiot. 49, 955-957.
13. Kinoshita, K., Takenaka, S., Suzuki, H., Morohoshi, T., and Hayashi, M. (1992). Mycinamicins, new macrolide antibiotics. XIII. isolation and structures of novel fermentation products from Micromonospora griseorubida (FERM BP-705). J. Antibiot. 45, 1-9.
14. Lombó, F., Gibson, M., Greenwell, L., Braña, A.F., Rohr, J., Salas, J.A., and Méndez, C. (2004). Engineering biosynthetic pathways. for deoxysugars: Branched-chain sugar pathways and derivatives from the antitumor tetracenomycin. Chem. Biol. 11, 1709-1718.
15. MacNeil, D.J., Gewain, K.M., Ruby, C.L., Dezeny, G., Gibbons, P.H., and MacNeil, T. (1992). Analysis of Streptomyces avermitilis genes required for avermectin biosynthesis utilizing a novel integration vector. Gene 111, 61-68.
16. Maki, M., and Renkonen, R. (2004). Biosynthesis of 6-deoxyhexose glycans in bacterial. Glycobiology 14, 1-15.
17. Mochizuki, S., Hiratsu, K., Suwa, M., Ishii, T., Sugino, F., Yamada, K., and Kinashi, H. (2003). The large linear plasmid pSLA2-L of Streptomyces rochei has an unusually condensed gene organization for secondary metabolism. Mol. Microbiol. 48, 1501-1510.
18. Ochsner, U.A., Fiechter, A., and Reiser, J. (1994). Isolation, characterization and expression in Escherichia coli of the Pseudomonas aeruginosa rhlAB genes encoding a rhamnosyltransferase involved in rhamnolipid bio-surfactant synthesis. J. Biol. Chem. 269, 19787-19795.
19. Quiros, L.M., and Salas, J.A. (1995). Biosynthesis of the macrolide oleandomycin by Streptomyces antibioticus. J. Biol. Chem. 270, 18234-18239.
20. Quiros, L.M., Carbajo, J.R., and Salas, J.A. (2000). Inversion of the anomeric configuration of the transferred sugar during inactivation of the macrolide antibiotic oleandomycin catalyzed by a macrolide glycosyltransferase. FEBS Lett. 476, 186-189.
21. Salah-Bey, K., Doumith, M., Michel, J.M., Haydock, S., Cortés, J., Leadlay, P. F., and Raynal, M.C. (1998). Targeted gene inactivaton for the elucidation of deoxysugar biosynthesis in the erythromycin producer Saccharopolyspora erythraea. Mol. Gen. Genet. 257, 542-553.
22. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989). Molecular cloning. A Laboratory Manual, 2nd ed. (NY, USA: Cold Spring Harbor, Cold Spring Harbor Laboratory).
23. Solenberg, P.J., Matsushima, P., Stack, D.R., Wilkie, S.C., Thompson, R.C., and Baltz, R.H. (1997). Production of hybrid glycopeptide antibiotics in vitro and in Streptomyces toyocaensis. Chem. Biol. 4, 195-202.
24. Tang, L., and McDaiel, R. (2001). Construction of desosamine containing polyketide libraries using a glycosyltransferase with broad substrate specificity. Chem. Biol. 8, 547-555.
25. Unligil, U.M., and Rini, J.M. (2000). Glycosyltransferase structure and mechanism. Curr. Opin. Struct. Biol. 10, 510-517.
26. Ward, S.L., Hu, Z., Schirmer, A, Reid, R., Revill, W.P., Reeves, C.D., Petrakovsky, O.V;, Dong, S.D., and Katz, L. (2004). Chalcomycin biosynthesis gene cluster from Streptomyces bikinensis: Novel feature of unusual ketolide produce through expression of chm polyketide synthase in Streptomyces fradiae. Antimicrob. Agents Chemother. 48, 4703-4712.
27. Wilson, V.T.W., and Cundliffe, E. (1998). Characterization and targeted disruption of a glycosyltransferase gene in the tylosin producer, Streptomyces fradiae. Gene 214, 95-100,
28. Woo, P.W.K., and Rubin, J.R. (1996). Chalcomycin: single-crystal X-ray crystallographic analysis; biosynthetic and stereochemical correlations with polyoxo macrolide antibiotics. Tetrahedron 52, 3857-3872.
29. Xue, Y., and Sherman, D.H. (2001). Biosynthesis and combinatorial biosynthesis of pikromycin-retated macrolides in Streptomyces venezuelae. Metab. Eng. 3, 15-26.