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Volumn 54, Issue 7, 2010, Pages 2830-2839

Glycosylation steps during spiramycin biosynthesis in Streptomyces ambofaciens: Involvement of three glycosyltransferases and their interplay with two auxiliary proteins

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; FOROCIDIN; FOROSAMINE; GLYCOSYLTRANSFERASE; MYCAMINOSE; MYCAROSE; NEOSPIRAMYCIN; SPIRAMYCIN; SUGAR; UNCLASSIFIED DRUG;

EID: 77953806325     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01602-09     Document Type: Article
Times cited : (36)

References (44)
  • 1
    • 0031006412 scopus 로고    scopus 로고
    • Antibiotic resistance gene cassettes derived from the omega interposon for use in E. coli and Streptomyces
    • Blondelet-Rouault, M. H., J. Weiser, A. Lebrihi, P. Branny, and J. L. Pernodet. 1997. Antibiotic resistance gene cassettes derived from the omega interposon for use in E. coli and Streptomyces. Gene 190:315-317.
    • (1997) Gene , vol.190 , pp. 315-317
    • Blondelet-Rouault, M.H.1    Weiser, J.2    Lebrihi, A.3    Branny, P.4    Pernodet, J.L.5
  • 2
    • 33746211329 scopus 로고    scopus 로고
    • Substrate specificity of the macrolide-glycosylating enzyme pair DesVII/DesVIII: Opportunities, limitations, and mechanistic hypotheses
    • Borisova, S. A., C. Zhang, H. Takahashi, H. Zhang, A. W. Wong, J. S. Thorson, and H. W. Liu. 2006. Substrate specificity of the macrolide- glycosylating enzyme pair DesVII/DesVIII: opportunities, limitations, and mechanistic hypotheses. Angew. Chem. Int. Ed. Engl. 45:2748-2753.
    • (2006) Angew. Chem. Int. Ed. Engl. , vol.45 , pp. 2748-2753
    • Borisova, S.A.1    Zhang, C.2    Takahashi, H.3    Zhang, H.4    Wong, A.W.5    Thorson, J.S.6    Liu, H.W.7
  • 3
    • 2542527641 scopus 로고    scopus 로고
    • Characterization of the glycosyltransferase activity of desVII: Analysis of and implications for the biosynthesis of macrolide antibiotics
    • Borisova, S. A., L. Zhao, I. C. Melancon, C. L. Kao, and H. W. Liu. 2004. Characterization of the glycosyltransferase activity of desVII: analysis of and implications for the biosynthesis of macrolide antibiotics. J. Am. Chem. Soc. 126:6534-6535.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6534-6535
    • Borisova, S.A.1    Zhao, L.2    Melancon, I.C.3    Kao, C.L.4    Liu, H.W.5
  • 4
    • 0035047003 scopus 로고    scopus 로고
    • Feedback control of polyketide metabolism during tylosin production
    • Butler, A. R., S. A. Flint, and E. Cundliffe. 2001. Feedback control of polyketide metabolism during tylosin production. Microbiology 147:795-801. (Pubitemid 32401319)
    • (2001) Microbiology , vol.147 , Issue.4 , pp. 795-801
    • Butler, A.R.1    Flint, S.A.2    Cundliffe, E.3
  • 5
    • 0034668869 scopus 로고    scopus 로고
    • A rapid method for efficient gene replacement in the filamentous fungus Aspergillus nidulans
    • Chaveroche, M. K., J. M. Ghigo, and C. d'Enfert. 2000. A rapid method for efficient gene replacement in the filamentous fungus Aspergillus nidulans. Nucleic Acids Res. 28:E97.
    • (2000) Nucleic Acids Res. , vol.28
    • Chaveroche, M.K.1    Ghigo, J.M.2    D'Enfert, C.3
  • 7
    • 0031437605 scopus 로고    scopus 로고
    • Stimulation of polyketide metabolism in Streptomyces fradiae by tylosin and its glycosylated precursors
    • Fish, S. A., and E. Cundliffe. 1997. Stimulation of polyketide metabolism in Streptomyces fradiae by tylosin and its glycosylated precursors. Microbiology 143:3871-3876.
    • (1997) Microbiology , vol.143 , pp. 3871-3876
    • Fish, S.A.1    Cundliffe, E.2
  • 8
    • 0026633027 scopus 로고
    • Characterization of a novel regulatory gene governing the expression of a polyketide synthase gene in Streptomyces ambofaciens
    • Geistlich, M., R. Losick, J. R. Turner, and R. N. Rao. 1992. Characterization of a novel regulatory gene governing the expression of a polyketide synthase gene in Streptomyces ambofaciens. Mol. Microbiol. 6:2019-2029.
    • (1992) Mol. Microbiol. , vol.6 , pp. 2019-2029
    • Geistlich, M.1    Losick, R.2    Turner, J.R.3    Rao, R.N.4
  • 9
    • 0031714973 scopus 로고    scopus 로고
    • Characterization of a glycosyl transferase inactivating macrolides, encoded by gimA from Streptomyces ambofaciens
    • Gourmelen, A., M. H. Blondelet-Rouault, and J. L. Pernodet. 1998. Characterization of a glycosyl transferase inactivating macrolides, encoded by gimA from Streptomyces ambofaciens. Antimicrob. Agents Chemother. 42:2612-2619.
    • (1998) Antimicrob. Agents Chemother. , vol.42 , pp. 2612-2619
    • Gourmelen, A.1    Blondelet-Rouault, M.H.2    Pernodet, J.L.3
  • 10
    • 0037452723 scopus 로고    scopus 로고
    • PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin
    • Gust, B., G. L. Challis, K. Fowler, T. Kieser, and K. F. Chater. 2003. PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. U. S. A. 100:1541-1546.
    • (2003) Proc. Natl. Acad. Sci. U. S. A. , vol.100 , pp. 1541-1546
    • Gust, B.1    Challis, G.L.2    Fowler, K.3    Kieser, T.4    Chater, K.F.5
  • 11
    • 0036342198 scopus 로고    scopus 로고
    • The structures of four macrolide antibiotics bound to the large ribosomal subunit
    • Hansen, J. L., J. A. Ippolito, N. Ban, P. Nissen, P. B. Moore, and T. A. Steitz. 2002. The structures of four macrolide antibiotics bound to the large ribosomal subunit. Mol. Cell 10:117-128.
    • (2002) Mol. Cell , vol.10 , pp. 117-128
    • Hansen, J.L.1    Ippolito, J.A.2    Ban, N.3    Nissen, P.4    Moore, P.B.5    Steitz, T.A.6
  • 12
    • 22544472151 scopus 로고    scopus 로고
    • The role of a second protein (DesVIII) in glycosylation for the biosynthesis of hybrid macrolide antibiotics in Streptomyces venezuelae
    • Hong, J. S. 2005. The role of a second protein (DesVIII) in glycosylation for the biosynthesis of hybrid macrolide antibiotics in Streptomyces venezuelae. J. Microbiol. Biotechnol. 15:640-645.
    • (2005) J. Microbiol. Biotechnol. , vol.15 , pp. 640-645
    • Hong, J.S.1
  • 13
    • 4444246615 scopus 로고    scopus 로고
    • New olivosyl derivatives of methymycin/pikromycin from an engineered strain of Streptomyces venezuelae
    • Hong, J. S., S. H. Park, C. Y. Choi, J. K. Sohng, and Y. J. Yoon. 2004. New olivosyl derivatives of methymycin/pikromycin from an engineered strain of Streptomyces venezuelae. FEMS Microbiol. Lett. 238:391-399.
    • (2004) FEMS Microbiol. Lett. , vol.238 , pp. 391-399
    • Hong, J.S.1    Park, S.H.2    Choi, C.Y.3    Sohng, J.K.4    Yoon, Y.J.5
  • 14
    • 33845512079 scopus 로고    scopus 로고
    • Functional analysis of desVIII homologues involved in glycosylation of macrolide antibiotics by interspecies complementation
    • Hong, J. S., S. J. Park, N. Parajuli, S. R. Park, H. S. Koh, W. S. Jung, C. Y. Choi, and Y. J. Yoon. 2007. Functional analysis of desVIII homologues involved in glycosylation of macrolide antibiotics by interspecies complementation. Gene 386:123-130.
    • (2007) Gene , vol.386 , pp. 123-130
    • Hong, J.S.1    Park, S.J.2    Parajuli, N.3    Park, S.R.4    Koh, H.S.5    Jung, W.S.6    Choi, C.Y.7    Yoon, Y.J.8
  • 15
    • 41849097831 scopus 로고    scopus 로고
    • In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa
    • Hong, L., Z. Zhao, C. E. Melancon III, H. Zhang, and H. W. Liu. 2008. In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa. J. Am. Chem. Soc. 130:4954-4967.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 4954-4967
    • Hong, L.1    Zhao, Z.2    Melancon III, C.E.3    Zhang, H.4    Liu, H.W.5
  • 16
    • 23144453475 scopus 로고    scopus 로고
    • SEARCHGTr: A program for analysis of glycosyltransferases involved in glycosylation of secondary metabolites
    • Kamra, P., R. S. Gokhale, and D. Mohanty. 2005. SEARCHGTr: a program for analysis of glycosyltransferases involved in glycosylation of secondary metabolites. Nucleic Acids Res. 33:W220-W225.
    • (2005) Nucleic Acids Res. , vol.33
    • Kamra, P.1    Gokhale, R.S.2    Mohanty, D.3
  • 19
    • 14844357497 scopus 로고    scopus 로고
    • Translation and protein synthesis: Macrolides
    • Katz, L., and G. W. Ashley. 2005. Translation and protein synthesis: macrolides. Chem. Rev. 105:499-528.
    • (2005) Chem. Rev. , vol.105 , pp. 499-528
    • Katz, L.1    Ashley, G.W.2
  • 21
    • 0030445331 scopus 로고    scopus 로고
    • Production of a novel polyketide through the construction of a hybrid polyketide synthase
    • Kuhstoss, S., M. Huber, J. R. Turner, J. W. Paschal, and R. N. Rao. 1996. Production of a novel polyketide through the construction of a hybrid polyketide synthase. Gene 183:231-236.
    • (1996) Gene , vol.183 , pp. 231-236
    • Kuhstoss, S.1    Huber, M.2    Turner, J.R.3    Paschal, J.W.4    Rao, R.N.5
  • 22
    • 0037069328 scopus 로고    scopus 로고
    • Resistance to the macrolide antibiotic tylosin is conferred by single methylations at 23S rRNA nucleotides G748 and A2058 acting in synergy
    • Liu, M., and S. Douthwaite. 2002. Resistance to the macrolide antibiotic tylosin is conferred by single methylations at 23S rRNA nucleotides G748 and A2058 acting in synergy. Proc. Natl. Acad. Sci. U. S. A. 99:14658-14663.
    • (2002) Proc. Natl. Acad. Sci. U. S. A. , vol.99 , pp. 14658-14663
    • Liu, M.1    Douthwaite, S.2
  • 23
    • 64249096506 scopus 로고    scopus 로고
    • Chapter 11. Sugar biosynthesis and modification
    • Lombo, F., C. Olano, J. A. Salas, and C. Mendez. 2009. Chapter 11. Sugar biosynthesis and modification. Methods Enzymol. 458:277-307.
    • (2009) Methods Enzymol. , vol.458 , pp. 277-307
    • Lombo, F.1    Olano, C.2    Salas, J.A.3    Mendez, C.4
  • 24
    • 19544377358 scopus 로고    scopus 로고
    • AknT is an activating protein for the glycosyltransferase AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin a
    • Lu, W., C. Leimkuhler, G. J. Gatto, Jr., R. G. Kruger, M. Oberthur, D. Kahne, and C. T. Walsh. 2005. AknT is an activating protein for the glycosyltransferase AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin A. Chem. Biol. 12:527-534.
    • (2005) Chem. Biol. , vol.12 , pp. 527-534
    • Lu, W.1    Leimkuhler, C.2    Gatto Jr., G.J.3    Kruger, R.G.4    Oberthur, M.5    Kahne, D.6    Walsh, C.T.7
  • 25
    • 11244310524 scopus 로고    scopus 로고
    • Characterization of tylM3/tylM2 and mydC/mycB pairs required for efficient glycosyltransfer in macrolide antibiotic biosynthesis
    • Melancon, C. E., III, H. Takahashi, and H. W. Liu. 2004. Characterization of tylM3/tylM2 and mydC/mycB pairs required for efficient glycosyltransfer in macrolide antibiotic biosynthesis. J. Am. Chem. Soc. 126:16726-16727.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 16726-16727
    • Melancon III, C.E.1    Takahashi, H.2    Liu, H.W.3
  • 26
    • 0035501490 scopus 로고    scopus 로고
    • Altering the glycosylation pattern of bioactive compounds
    • Mendez, C., and J. A. Salas. 2001. Altering the glycosylation pattern of bioactive compounds. Trends Biotechnol. 19:449-456.
    • (2001) Trends Biotechnol. , vol.19 , pp. 449-456
    • Mendez, C.1    Salas, J.A.2
  • 27
    • 0023892552 scopus 로고
    • A novel suicide vector and its use in construction of insertion mutations: Osmoregulation of outer membrane proteins and virulence determinants in Vibrio cholerae requires toxR
    • Miller, V. L., and J. J. Mekalanos. 1988. A novel suicide vector and its use in construction of insertion mutations: osmoregulation of outer membrane proteins and virulence determinants in Vibrio cholerae requires toxR. J. Bacteriol. 170:2575-2583.
    • (1988) J. Bacteriol. , vol.170 , pp. 2575-2583
    • Miller, V.L.1    Mekalanos, J.J.2
  • 28
    • 0022388597 scopus 로고
    • Structure activity relationships of spiramycins
    • Omura, S., H. Sano, and T. Sunazuka. 1985. Structure activity relationships of spiramycins. J. Antimicrob. Chemother. 16(Suppl. A):1-11.
    • (1985) J. Antimicrob. Chemother. , vol.16 , Issue.SUPPL. A , pp. 1-11
    • Omura, S.1    Sano, H.2    Sunazuka, T.3
  • 29
    • 0027192079 scopus 로고
    • Resistance to spiramycin in Streptomyces ambofaciens, the producer organism, involves at least two different mechanisms
    • Pernodet, J. L., M. T. Alegre, M. H. Blondelet-Rouault, and M. Guerineau. 1993. Resistance to spiramycin in Streptomyces ambofaciens, the producer organism, involves at least two different mechanisms. J. Gen. Microbiol. 139:1003-1011.
    • (1993) J. Gen. Microbiol. , vol.139 , pp. 1003-1011
    • Pernodet, J.L.1    Alegre, M.T.2    Blondelet-Rouault, M.H.3    Guerineau, M.4
  • 30
    • 0030026827 scopus 로고    scopus 로고
    • The macrolide-lincosamide-streptogramin B resistance phenotypes characterized by using a specifically deleted, antibiotic-sensitive strain of Streptomyces lividans
    • Pernodet, J. L., S. Fish, M. H. Blondelet-Rouault, and E. Cundliffe. 1996. The macrolide-lincosamide-streptogramin B resistance phenotypes characterized by using a specifically deleted, antibiotic-sensitive strain of Streptomyces lividans. Antimicrob. Agents Chemother. 40:581-585.
    • (1996) Antimicrob. Agents Chemother. , vol.40 , pp. 581-585
    • Pernodet, J.L.1    Fish, S.2    Blondelet-Rouault, M.H.3    Cundliffe, E.4
  • 31
    • 0021592032 scopus 로고
    • In vitro insertional mutagenesis with a selectable DNA fragment
    • Prentki, P., and H. M. Krisch. 1984. In vitro insertional mutagenesis with a selectable DNA fragment. Gene 29:303-313.
    • (1984) Gene , vol.29 , pp. 303-313
    • Prentki, P.1    Krisch, H.M.2
  • 32
    • 0031799094 scopus 로고    scopus 로고
    • Two glycosyltransferases and a glycosidase are involved in oleandomycin modification during its biosynthesis by Streptomyces antibioticus
    • Quiros, L. M., I. Aguirrezabalaga, C. Olano, C. Mendez, and J. A. Salas. 1998. Two glycosyltransferases and a glycosidase are involved in oleandomycin modification during its biosynthesis by Streptomyces antibioticus. Mol. Microbiol. 28:1177-1185.
    • (1998) Mol. Microbiol. , vol.28 , pp. 1177-1185
    • Quiros, L.M.1    Aguirrezabalaga, I.2    Olano, C.3    Mendez, C.4    Salas, J.A.5
  • 34
    • 0036774667 scopus 로고    scopus 로고
    • Modification of post-PKS tailoring steps through combinatorial biosynthesis
    • Rix, U., C. Fischer, L. L. Remsing, and J. Rohr. 2002. Modification of post-PKS tailoring steps through combinatorial biosynthesis. Nat. Prod. Rep. 19:542-580.
    • (2002) Nat. Prod. Rep. , vol.19 , pp. 542-580
    • Rix, U.1    Fischer, C.2    Remsing, L.L.3    Rohr, J.4
  • 36
    • 34247511117 scopus 로고    scopus 로고
    • Engineering the glycosylation of natural products in actinomycetes
    • Salas, J. A., and C. Mendez. 2007. Engineering the glycosylation of natural products in actinomycetes. Trends Microbiol. 15:219-232.
    • (2007) Trends Microbiol. , vol.15 , pp. 219-232
    • Salas, J.A.1    Mendez, C.2
  • 38
    • 0035950132 scopus 로고    scopus 로고
    • Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria
    • Schlunzen, F., R. Zarivach, J. Harms, A. Bashan, A. Tocilj, R. Albrecht, A. Yonath, and F. Franceschi. 2001. Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature 413:814-821.
    • (2001) Nature , vol.413 , pp. 814-821
    • Schlunzen, F.1    Zarivach, R.2    Harms, J.3    Bashan, A.4    Tocilj, A.5    Albrecht, R.6    Yonath, A.7    Franceschi, F.8
  • 39
    • 0021027842 scopus 로고
    • A broad host range mobilization system for in vivo genetic engineering: Transposon mutagenesis in Gram negative bacteria
    • Simon, R., U. Priefer, and A. Puhler. 1983. A broad host range mobilization system for in vivo genetic engineering: transposon mutagenesis in Gram negative bacteria. Nat. Biotechnol. 1:784-791.
    • (1983) Nat. Biotechnol. , vol.1 , pp. 784-791
    • Simon, R.1    Priefer, U.2    Puhler, A.3
  • 40
    • 0035160878 scopus 로고    scopus 로고
    • Macrolide resistance conferred by base substitutions in 23S rRNA
    • Vester, B., and S. Douthwaite. 2001. Macrolide resistance conferred by base substitutions in 23S rRNA. Antimicrob. Agents Chemother. 45:1-12.
    • (2001) Antimicrob. Agents Chemother. , vol.45 , pp. 1-12
    • Vester, B.1    Douthwaite, S.2
  • 41
    • 0033852319 scopus 로고    scopus 로고
    • Biosynthesis of the anti-parasitic agent megalomicin: Transformation of erythromycin to megalomicin in Saccharopolyspora erythraea
    • Volchegursky, Y., Z. Hu, L. Katz, and R. McDaniel. 2000. Biosynthesis of the anti-parasitic agent megalomicin: transformation of erythromycin to megalomicin in Saccharopolyspora erythraea. Mol. Microbiol. 37:752-762.
    • (2000) Mol. Microbiol. , vol.37 , pp. 752-762
    • Volchegursky, Y.1    Hu, Z.2    Katz, L.3    McDaniel, R.4
  • 44
    • 26844543758 scopus 로고    scopus 로고
    • In vitro reconstitution of EryCIII activity for the preparation of unnatural macrolides
    • Yuan, Y., H. S. Chung, C. Leimkuhler, C. T. Walsh, D. Kahne, and S. Walker. 2005. In vitro reconstitution of EryCIII activity for the preparation of unnatural macrolides. J. Am. Chem. Soc. 127:14128-14129.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14128-14129
    • Yuan, Y.1    Chung, H.S.2    Leimkuhler, C.3    Walsh, C.T.4    Kahne, D.5    Walker, S.6


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