메뉴 건너뛰기




Volumn 9, Issue 12, 2002, Pages 1305-1314

Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DRUG DERIVATIVE; GLUCOSE; GLUCOSYLTRANSFERASE; GLUCOSYLTRANSFERASE D; GLUCOSYLTRANSFERASE E; GLYCOPEPTIDE; TEICOPLANIN; VANCOMYCIN;

EID: 12244297801     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(02)00270-3     Document Type: Article
Times cited : (142)

References (46)
  • 2
    • 0029863413 scopus 로고    scopus 로고
    • Regulation of VanB-type vancomycin resistance gene expression by the VanS(B)-VanR (B) two-component regulatory system in Enterococcus faecalis V583
    • Evers S., Courvalin P. Regulation of VanB-type vancomycin resistance gene expression by the VanS(B)-VanR (B) two-component regulatory system in Enterococcus faecalis V583. J. Bacteriol. 178:1996;1302-1309.
    • (1996) J. Bacteriol. , vol.178 , pp. 1302-1309
    • Evers, S.1    Courvalin, P.2
  • 3
    • 0027328589 scopus 로고
    • Vancomycin resistance: Decoding the molecular logic
    • Walsh C.T. Vancomycin resistance. decoding the molecular logic Science. 261:1993;308-309.
    • (1993) Science , vol.261 , pp. 308-309
    • Walsh, C.T.1
  • 4
    • 0026355435 scopus 로고
    • Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: Biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA
    • Bugg T.D., Wright G.D., Dutka-Malen S., Arthur M., Courvalin P., Walsh C.T. Molecular basis for vancomycin resistance in Enterococcus faecium BM4147. biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA Biochemistry. 30:1991;10408-10415.
    • (1991) Biochemistry , vol.30 , pp. 10408-10415
    • Bugg, T.D.1    Wright, G.D.2    Dutka-Malen, S.3    Arthur, M.4    Courvalin, P.5    Walsh, C.T.6
  • 5
    • 0027475726 scopus 로고
    • Toward an estimation of binding constants in aqueous solution: Studies of associations of vancomycin group antibiotics
    • Williams D.H., Searle M.S., Mackay J.P., Gerhard U., Maplestone R.A. Toward an estimation of binding constants in aqueous solution. studies of associations of vancomycin group antibiotics Proc. Natl. Acad. Sci. USA. 90:1993;1172-1178.
    • (1993) Proc. Natl. Acad. Sci. USA , vol.90 , pp. 1172-1178
    • Williams, D.H.1    Searle, M.S.2    Mackay, J.P.3    Gerhard, U.4    Maplestone, R.A.5
  • 9
    • 0035901490 scopus 로고    scopus 로고
    • Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: Novel glycopeptides
    • Losey H.C., Peczuh M.W., Chen Z., Eggert U.S., Dong S.D., Pelczer I., Kahne D., Walsh C.T. Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones. novel glycopeptides Biochemistry. 40:2001;4745-4755.
    • (2001) Biochemistry , vol.40 , pp. 4745-4755
    • Losey, H.C.1    Peczuh, M.W.2    Chen, Z.3    Eggert, U.S.4    Dong, S.D.5    Pelczer, I.6    Kahne, D.7    Walsh, C.T.8
  • 10
    • 0035501490 scopus 로고    scopus 로고
    • Altering the glycosylation pattern of bioactive compounds
    • Mendez C., Salas J.A. Altering the glycosylation pattern of bioactive compounds. Trends Biotechnol. 19:2001;449-456.
    • (2001) Trends Biotechnol. , vol.19 , pp. 449-456
    • Mendez, C.1    Salas, J.A.2
  • 11
    • 0035075686 scopus 로고    scopus 로고
    • Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin
    • Blanco G., Patallo E.P., Brana A.F., Trefzer A., Bechthold A., Rohr J., Mendez C., Salas J.A. Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin. Chem. Biol. 8:2001;253-263.
    • (2001) Chem. Biol. , vol.8 , pp. 253-263
    • Blanco, G.1    Patallo, E.P.2    Brana, A.F.3    Trefzer, A.4    Bechthold, A.5    Rohr, J.6    Mendez, C.7    Salas, J.A.8
  • 14
    • 0034044582 scopus 로고    scopus 로고
    • Generation of hybrid elloramycin analogs by combinatorial biosynthesis using genes from anthracycline-type and macrolide biosynthetic pathways
    • Rodriguez L., Oelkers C., Aguirrezabalaga I., Brana A.F., Rohr J., Mendez C., Salas J.A. Generation of hybrid elloramycin analogs by combinatorial biosynthesis using genes from anthracycline-type and macrolide biosynthetic pathways. J. Mol. Microbiol. Biotechnol. 2:2000;271-276.
    • (2000) J. Mol. Microbiol. Biotechnol. , vol.2 , pp. 271-276
    • Rodriguez, L.1    Oelkers, C.2    Aguirrezabalaga, I.3    Brana, A.F.4    Rohr, J.5    Mendez, C.6    Salas, J.A.7
  • 16
    • 0034686686 scopus 로고    scopus 로고
    • A general enzymatic method for the synthesis of natural and unnatural UDP- and TDP-nucleotide sugars
    • Jiang J., Biggins J.B., Thorson J.S. A general enzymatic method for the synthesis of natural and unnatural UDP- and TDP-nucleotide sugars. J. Am. Chem. Soc. 122:2000;6803-6804.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6803-6804
    • Jiang, J.1    Biggins, J.B.2    Thorson, J.S.3
  • 17
    • 0035901648 scopus 로고    scopus 로고
    • Expanding the pyrimidine diphosphosugar repertoire: The chemoenzymatic synthesis of amino- and acetamidoglucopyranosyl derivatives
    • Jiang J., Biggins J.B., Thorson J.S. Expanding the pyrimidine diphosphosugar repertoire. the chemoenzymatic synthesis of amino- and acetamidoglucopyranosyl derivatives Angew. Chem. Int. Ed. Engl. 40:2001;1502-1505.
    • (2001) Angew. Chem. Int. Ed. Engl. , vol.40 , pp. 1502-1505
    • Jiang, J.1    Biggins, J.B.2    Thorson, J.S.3
  • 18
    • 0030956956 scopus 로고    scopus 로고
    • 1H-tetrazole as catalyst in phosphoromorpholidate coupling reactions: Efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose
    • 1H-tetrazole as catalyst in phosphoromorpholidate coupling reactions. efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose J. Org. Chem. 62:1997;2144-2147.
    • (1997) J. Org. Chem. , vol.62 , pp. 2144-2147
    • Wittmann, V.1    Wong, C.-H.2
  • 19
    • 0019880383 scopus 로고
    • Active transport of charged substrates by a proton/sugar co-transport system. Amino-sugar uptake in the yeast Rhodotorula gracilis
    • Niemietz C., Hauer R., Hofer M. Active transport of charged substrates by a proton/sugar co-transport system. Amino-sugar uptake in the yeast Rhodotorula gracilis. Biochem. J. 194:1981;433-441.
    • (1981) Biochem. J. , vol.194 , pp. 433-441
    • Niemietz, C.1    Hauer, R.2    Hofer, M.3
  • 20
    • 0025863973 scopus 로고
    • Phosphorylated aminosugars: Synthesis, properties, and reactivity in enzymatic reactions
    • Sem D.S., Cleland W.W. Phosphorylated aminosugars. synthesis, properties, and reactivity in enzymatic reactions Biochemistry. 30:1991;4978-4984.
    • (1991) Biochemistry , vol.30 , pp. 4978-4984
    • Sem, D.S.1    Cleland, W.W.2
  • 21
    • 0034710989 scopus 로고    scopus 로고
    • Deoxysugars in glycopeptide antibiotics: Enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis
    • Chen H., Thomas M.G., Hubbard B.L., Losey H.C., Walsh C.T., Burkart M.D. Deoxysugars in glycopeptide antibiotics. enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis Proc. Natl. Acad. Sci. USA. 97:2000;11942-11947.
    • (2000) Proc. Natl. Acad. Sci. USA , vol.97 , pp. 11942-11947
    • Chen, H.1    Thomas, M.G.2    Hubbard, B.L.3    Losey, H.C.4    Walsh, C.T.5    Burkart, M.D.6
  • 22
    • 0038527474 scopus 로고    scopus 로고
    • Vancomycin: Conformational consequences of the sugar substituent
    • Grdadolnik S.G., Pristovsek P., Mierke D.F. Vancomycin. conformational consequences of the sugar substituent J. Med. Chem. 41:1998;2090-2099.
    • (1998) J. Med. Chem. , vol.41 , pp. 2090-2099
    • Grdadolnik, S.G.1    Pristovsek, P.2    Mierke, D.F.3
  • 23
    • 0023903812 scopus 로고
    • Function of the amino sugar and N-terminal amino acid of the antibiotic vancomycin in its complexation with cell wall peptides
    • Kannan R., Harris C.H., Harris T.M., Waltho J.P., Skelton N.J., Williams D.H. Function of the amino sugar and N-terminal amino acid of the antibiotic vancomycin in its complexation with cell wall peptides. J. Am. Chem. Soc. 110:1988;2946-2953.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2946-2953
    • Kannan, R.1    Harris, C.H.2    Harris, T.M.3    Waltho, J.P.4    Skelton, N.J.5    Williams, D.H.6
  • 25
    • 0028853826 scopus 로고
    • Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyltransferase involved in daunorubicin biosynthesis
    • Otten S.L., Liu X., Ferguson J., Hutchinson C.R. Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyltransferase involved in daunorubicin biosynthesis. J. Bacteriol. 177:1995;6688-6692.
    • (1995) J. Bacteriol. , vol.177 , pp. 6688-6692
    • Otten, S.L.1    Liu, X.2    Ferguson, J.3    Hutchinson, C.R.4
  • 26
    • 0033852319 scopus 로고    scopus 로고
    • Biosynthesis of the anti-parasitic agent megalomicin: Transformation of erythromycin to megalomicin in Saccharopolyspora erythraea
    • Volchegursky Y., Hu Z., Katz L., McDaniel R. Biosynthesis of the anti-parasitic agent megalomicin. transformation of erythromycin to megalomicin in Saccharopolyspora erythraea Mol. Microbiol. 37:2000;752-762.
    • (2000) Mol. Microbiol. , vol.37 , pp. 752-762
    • Volchegursky, Y.1    Hu, Z.2    Katz, L.3    McDaniel, R.4
  • 27
    • 0345643323 scopus 로고    scopus 로고
    • Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908
    • Pelzer S., Sussmuth 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. 43:1999;1565-1573.
    • (1999) Antimicrob. Agents Chemother. , vol.43 , pp. 1565-1573
    • Pelzer, S.1    Sussmuth, R.2    Heckmann, D.3    Recktenwald, J.4    Huber, P.5    Jung, G.6    Wohlleben, W.7
  • 30
    • 0035022268 scopus 로고    scopus 로고
    • Nature's carbohydrate chemists: The enzymatic glycosylation of bioactive bacterial metabolites
    • Thorson J.S., Hoster T.J., Jiang J., Biggins J.B., Ahlert J. Nature's carbohydrate chemists. the enzymatic glycosylation of bioactive bacterial metabolites Curr. Org. Chem. 5:2001;139-167.
    • (2001) Curr. Org. Chem. , vol.5 , pp. 139-167
    • Thorson, J.S.1    Hoster, T.J.2    Jiang, J.3    Biggins, J.B.4    Ahlert, J.5
  • 32
    • 0027998112 scopus 로고
    • Pathways and mechanisms in the biogenesis of novel deoxysugars by bacteria
    • Liu H.W., Thorson J.S. Pathways and mechanisms in the biogenesis of novel deoxysugars by bacteria. Annu. Rev. Microbiol. 48:1994;223-256.
    • (1994) Annu. Rev. Microbiol. , vol.48 , pp. 223-256
    • Liu, H.W.1    Thorson, J.S.2
  • 36
    • 0034938546 scopus 로고    scopus 로고
    • Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics
    • Mulichak A.M., Losey H.C., Walsh C.T., Garavito R.M. Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics. Structure. 9:2001;547-557.
    • (2001) Structure , vol.9 , pp. 547-557
    • Mulichak, A.M.1    Losey, H.C.2    Walsh, C.T.3    Garavito, R.M.4
  • 37
    • 0033623762 scopus 로고    scopus 로고
    • The 1.9 A crystal structure of Escherichia coli MurG, a membrane-associated glycosyltransferase involved in peptidoglycan biosynthesis
    • Ha S., Walker D., Shi Y., Walker S. The 1.9 A crystal structure of Escherichia coli MurG, a membrane-associated glycosyltransferase involved in peptidoglycan biosynthesis. Protein Sci. 9:2000;1045-1052.
    • (2000) Protein Sci. , vol.9 , pp. 1045-1052
    • Ha, S.1    Walker, D.2    Shi, Y.3    Walker, S.4
  • 38
    • 0031900477 scopus 로고    scopus 로고
    • Analysis of eryBI, eryBIII and eryBVII from the erythromycin biosynthetic gene cluster in Saccharopolyspora erythraea
    • Gaisser S., Bohm G.A., Doumith M., Raynal M.C., Dhillon N., Cortes J., Leadlay P.F. Analysis of eryBI, eryBIII and eryBVII from the erythromycin biosynthetic gene cluster in Saccharopolyspora erythraea. Mol. Gen. Genet. 258:1998;78-88.
    • (1998) Mol. Gen. Genet. , vol.258 , pp. 78-88
    • Gaisser, S.1    Bohm, G.A.2    Doumith, M.3    Raynal, M.C.4    Dhillon, N.5    Cortes, J.6    Leadlay, P.F.7
  • 39
    • 0031013034 scopus 로고    scopus 로고
    • Analysis of four tylosin biosynthetic genes from the tylLM region of the Streptomyces fradiae genome
    • Gandecha A.R., Large S.L., Cundliffe E. Analysis of four tylosin biosynthetic genes from the tylLM region of the Streptomyces fradiae genome. Gene. 184:1997;197-203.
    • (1997) Gene , vol.184 , pp. 197-203
    • Gandecha, A.R.1    Large, S.L.2    Cundliffe, E.3
  • 40
    • 0037140766 scopus 로고    scopus 로고
    • Rationally designed glycosylated premithramycins: Hybrid aromatic polyketides using genes from three different biosynthetic pathways
    • Trefzer A., Blanco G., Remsing L., Kunzel E., Rix U., Lipata F., Brana A.F., Mendez 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.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6056-6062
    • Trefzer, A.1    Blanco, G.2    Remsing, L.3    Kunzel, E.4    Rix, U.5    Lipata, F.6    Brana, A.F.7    Mendez, C.8    Rohr, J.9    Bechthold, A.10
  • 41
    • 0001505263 scopus 로고
    • Synthesis of deoxyhalogeno sugars. Reaction of halide ions, with 1,2,3,4-tetra-O-acetyl-6-O-[(trifluoromethyl)sulfonyl]-β-D-glucopyranose
    • Ambrose M.G., Binkley R.W. Synthesis of deoxyhalogeno sugars. Reaction of halide ions, with 1,2,3,4-tetra-O-acetyl-6-O-[(trifluoromethyl)sulfonyl]-β-D- glucopyranose. J. Org. Chem. 48:1983;674-677.
    • (1983) J. Org. Chem. , vol.48 , pp. 674-677
    • Ambrose, M.G.1    Binkley, R.W.2
  • 43
    • 33748650843 scopus 로고    scopus 로고
    • Internally quenched fluorogenic, alpha-helical dimeric peptides and glycopeptides for the evaluation of the effect of glycosylation on the conformation of peptides
    • Mehta S., Meldal M., Ferro V., Duus J.O., Bock K. Internally quenched fluorogenic, alpha-helical dimeric peptides and glycopeptides for the evaluation of the effect of glycosylation on the conformation of peptides. J. Chem. Soc. [Perkin. 1] 1:1997;1365-1374.
    • (1997) J. Chem. Soc. [Perkin 1] , vol.1 , pp. 1365-1374
    • Mehta, S.1    Meldal, M.2    Ferro, V.3    Duus, J.O.4    Bock, K.5
  • 44
    • 0026428314 scopus 로고
    • A short synthesis of 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-β-D- glucopyranose and the corresponding α-glucosyl chloride from D-mannose
    • Pavliak V., Kovac P. A short synthesis of 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-β-D- glucopyranose and the corresponding α-glucosyl chloride from D-mannose. Carbohydr. Res. 210:1991;333-337.
    • (1991) Carbohydr. Res. , vol.210 , pp. 333-337
    • Pavliak, V.1    Kovac, P.2
  • 45
    • 0033529841 scopus 로고    scopus 로고
    • Stereospecific solution- and solid-phase glycosylations. Synthesis of β-linked saccharides and construction of disaccharide libraries using phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides as glycosyl donors
    • Silva D.J., Wang H., Allanson N.M., Jain R.K., Sofia M.J. Stereospecific solution- and solid-phase glycosylations. Synthesis of β-linked saccharides and construction of disaccharide libraries using phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides as glycosyl donors. J. Org. Chem. 64:1999;5926-5929.
    • (1999) J. Org. Chem. , vol.64 , pp. 5926-5929
    • Silva, D.J.1    Wang, H.2    Allanson, N.M.3    Jain, R.K.4    Sofia, M.J.5
  • 46
    • 0035925014 scopus 로고    scopus 로고
    • Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns (3,4,5)P3] and its diastereoisomers
    • Gaffney P.R.J., Reese C.B. Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns (3,4,5)P3] and its diastereoisomers. J. Chem. Soc. [Perkin. 1] 1:2001;192-205.
    • (2001) J. Chem. Soc. [Perkin 1] , vol.1 , pp. 192-205
    • Gaffney, P.R.J.1    Reese, C.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.