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Volumn 64, Issue 1, 2011, Pages 103-109

Enzymatic synthesis of vancomycin derivatives using galactosyltransferase and sialyltransferase

Author keywords

enzymatic synthesis; glycosyltransferase; sialic acid; vancomycin

Indexed keywords

ALPHA2,3 SIALYLTRANSFERASE; BETA1,4 GALACTOSYLTRANSFERASE; GALACTOSYLTRANSFERASE; SIALYLTRANSFERASE; UNCLASSIFIED DRUG; VANCOMYCIN DERIVATIVE;

EID: 79251629981     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.131     Document Type: Article
Times cited : (24)

References (26)
  • 1
    • 0017802490 scopus 로고
    • Structure of vancomycin and its complex with acetyl-D-alanyl-D-alanine
    • Sheldrick, G. M., Jones, P. G., Kennard, O., Williams, D. H. & Smith, G. A. Structure of vancomycin and its complex with acetyl-D-alanyl-D-alanine. Nature 271, 223-225 (1978).
    • (1978) Nature , vol.271 , pp. 223-225
    • Sheldrick, G.M.1    Jones, P.G.2    Kennard, O.3    Williams, D.H.4    Smith, G.A.5
  • 2
    • 0019786984 scopus 로고
    • Structure revision of the antibiotic vancomycin. The use of nuclear overhauser effect difference spectroscopy
    • Williamson, M. P. & Williams, D. H. Structure revision of the antibiotic vancomycin. The use of nuclear overhauser effect difference spectroscopy. J. Am. Chem. Soc. 103, 6580-6585 (1981).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6580-6585
    • Williamson, M.P.1    Williams, D.H.2
  • 3
    • 0023676889 scopus 로고
    • Selective cleavage of vancosamine, glucose, and N-methyl-leucine from vancomycin and related antibiotics
    • Nagarajan, R. & Schabel, A. A. Selective cleavage of vancosamine, glucose, and N-methyl-leucine from vancomycin and related antibiotics. J. Chem. Soc. Chem. Commun. 1306-1307 (1988).
    • (1988) J. Chem. Soc. Chem. Commun. , pp. 1306-1307
    • Nagarajan, R.1    Schabel, A.A.2
  • 4
    • 0034710989 scopus 로고    scopus 로고
    • Deoxysugar in glycopeptides antibiotics: Enzymatic synthesis of TDP-Lepivancosamine in chloroeremomycin biosynthesis
    • Chen, H. et al. Deoxysugar in glycopeptides antibiotics: Enzymatic synthesis of TDP-Lepivancosamine in chloroeremomycin biosynthesis. Proc. Natl Acad. Sci. USA 97, 11942-11947 (2000).
    • (2000) Proc. Natl Acad. Sci. USA , vol.97 , pp. 11942-11947
    • Chen, H.1
  • 5
    • 12244297801 scopus 로고    scopus 로고
    • Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides
    • Losey, H. C. et al. Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides. Chem. Biol. 9, 1305-1314 (2002).
    • (2002) Chem. Biol. , vol.9 , pp. 1305-1314
    • Losey, H.C.1
  • 6
    • 1842428817 scopus 로고    scopus 로고
    • Characterization of a regiospecifi epivancosaminyltransferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin
    • Lu,W. et al. Characterization of a regiospecifi epivancosaminyltransferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin. Proc. Natl Acad. Sci. USA 101, 4390-4395 (2004).
    • (2004) Proc. Natl Acad. Sci. USA , vol.101 , pp. 4390-4395
    • Lu, W.1
  • 7
    • 23044507077 scopus 로고    scopus 로고
    • A systematic investigation of the synthetic utility of glycopeptide glycosyltransferases
    • Oberthur, M . et al. A systematic investigation of the synthetic utility of glycopeptide glycosyltransferases. J. Am. Chem. Soc. 127, 10747-10752 (2005).
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10747-10752
    • Oberthur, M.1
  • 8
    • 17844409813 scopus 로고    scopus 로고
    • Diversifying vancomycin via chemoenzymatic strategies
    • Fu, X., Albermann, C., Zhang, C. & Thorson, J. S. Diversifying vancomycin via chemoenzymatic strategies. Org. Lett. 7, 1513-1515 (2005).
    • (2005) Org. Lett. , vol.7 , pp. 1513-1515
    • Fu, X.1    Albermann, C.2    Zhang, C.3    Thorson, J.S.4
  • 9
    • 0033624155 scopus 로고    scopus 로고
    • Cloning and expression of β1,4- galactosyltransferase gene from Helicobacter pylori
    • Endo, T., Koizumi, S., Tabata, K. & Ozaki, A. Cloning and expression of β1,4- galactosyltransferase gene from Helicobacter pylori. Glycobiology 10, 809-813 (2000).
    • (2000) Glycobiology , vol.10 , pp. 809-813
    • Endo, T.1    Koizumi, S.2    Tabata, K.3    Ozaki, A.4
  • 10
    • 0034012150 scopus 로고    scopus 로고
    • Functional genomics of Helicobacter pylori: Identification of a β-1,4 galactosyltransferase and generation of mutants with altered lipopolysaccharide
    • Logan, S. M., Conlan, J. W., Monteiro, M.A., Wakarchuk, W.W. & Altman, E. Functional genomics of Helicobacter pylori: Identification of a β-1,4 galactosyltransferase and generation of mutants with altered lipopolysaccharide. Mol. Microbiol. 35, 1156-1167 (2000).
    • (2000) Mol. Microbiol. , vol.35 , pp. 1156-1167
    • Logan, S.M.1    Conlan, J.W.2    Monteiro, M.A.3    Wakarchuk, W.W.4    Altman, E.5
  • 11
    • 0037393072 scopus 로고    scopus 로고
    • P1 trisaccharide (Galα1,4- Galβ1,4GlcNAc) synthesis by enzyme glycosylation reactions using recombinant Escherichia coli
    • Liu, Z., Lu, Y ., Zhang, J., Pardee, K. & Wang, P. G. P1 trisaccharide (Galα1,4- Galβ1,4GlcNAc) synthesis by enzyme glycosylation reactions using recombinant Escherichia coli. Appl. Environ. Microbiol. 69, 2110-2115 (2003).
    • (2003) Appl. Environ. Microbiol. , vol.69 , pp. 2110-2115
    • Liu, Z.1    Lu, Y.2    Zhang, J.3    Pardee, K.4    Wang, P.G.5
  • 12
    • 29344431622 scopus 로고    scopus 로고
    • A multifunctional Pasteurella multocida sialyltransferase: A powerful tool for the synthesis of sialoside libraries
    • Yu, H . et al. A multifunctional Pasteurella multocida sialyltransferase: A powerful tool for the synthesis of sialoside libraries. J. Am. Chem. Soc. 127, 17618-17619 (2005).
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 17618-17619
    • Yu, H.1
  • 13
    • 0033574743 scopus 로고    scopus 로고
    • Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala
    • Ge, M. et al. Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala. Science 284, 507-511 (1999).
    • (1999) Science , vol.284 , pp. 507-511
    • Ge, M.1
  • 14
    • 0347384092 scopus 로고    scopus 로고
    • Antibiotic optimization via invitro glycorandomization
    • Fu, X. et al. Antibiotic optimization via invitro glycorandomization. Nat. Biotechnol. 21, 1467-1469 (2003).
    • (2003) Nat. Biotechnol. , vol.21 , pp. 1467-1469
    • Fu, X.1
  • 15
    • 0035840941 scopus 로고    scopus 로고
    • An efficient chemoenzymatic strategy for the synthesis of wild-type and vancomycin-resistant bacterial cell-wall precursors: UDP-N-acetylmuramyl peptides
    • Liu, H., Sadamoto, R., Sears, P. S. & Wong, C. H. An efficient chemoenzymatic strategy for the synthesis of wild-type and vancomycin-resistant bacterial cell-wall precursors: UDP-N-acetylmuramyl peptides. J. Am. Chem. Soc. 123, 9916-9917 (2001).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9916-9917
    • Liu, H.1    Sadamoto, R.2    Sears, P.S.3    Wong, C.H.4
  • 16
    • 0037019542 scopus 로고    scopus 로고
    • Atropselective macrocyclization of diaryl ether ring systems: Application to the synthesis of vancomycin model systems
    • Nicolaou, K. C. & Boddy, C. N. Atropselective macrocyclization of diaryl ether ring systems: Application to the synthesis of vancomycin model systems. J. Am. Chem. Soc. 124, 10451-10455 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10451-10455
    • Nicolaou, K.C.1    Boddy, C.N.2
  • 17
    • 33749171560 scopus 로고    scopus 로고
    • Vancomycin analogues containing monosaccharides exhibit improved antibiotic activity: A combined one-pot enzymatic glycosylation and chemical diversification strategy
    • Thayer, D. A. & Wong, C. H. Vancomycin analogues containing monosaccharides exhibit improved antibiotic activity: A combined one-pot enzymatic glycosylation and chemical diversification strategy. Chem Asian J 1, 445-452 (2006).
    • (2006) Chem Asian J , vol.1 , pp. 445-452
    • Thayer, D.A.1    Wong, C.H.2
  • 19
    • 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, 2090-2099 (1998).
    • (1998) J. Med. Chem. , vol.41 , pp. 2090-2099
    • Grdadolnik, S.G.1    Pristovsek, P.2    Mierke, D.F.3
  • 20
    • 0034444960 scopus 로고    scopus 로고
    • Achievements and challenges of sialic acid research
    • Schauer, R. Achievements and challenges of sialic acid research. Glycoconj J 17, 485-499 (2000).
    • (2000) Glycoconj J , vol.17 , pp. 485-499
    • Schauer, R.1
  • 21
    • 0036462606 scopus 로고    scopus 로고
    • Chemical diversity in the sialic acids and related alpha-keto acids: An evolutionary perspective
    • Angata, T. & Varki, A. Chemical diversity in the sialic acids and related alpha-keto acids: An evolutionary perspective. Chem. Rev. 102, 439-469 (2002).
    • (2002) Chem. Rev. , vol.102 , pp. 439-469
    • Angata, T.1    Varki, A.2
  • 23
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254 (1976).
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 24
    • 48649087365 scopus 로고    scopus 로고
    • A β-1,4-galactosyltransferase from Helicobacter pylori is an efficient and versatile biocatalyst displaying a novel activity for thioglycoside synthesis
    • Namdjou, D. J. et al. A β-1,4-galactosyltransferase from Helicobacter pylori is an efficient and versatile biocatalyst displaying a novel activity for thioglycoside synthesis. Chem. BioChem. 9, 1632-1640 (2008).
    • (2008) Chem. BioChem. , vol.9 , pp. 1632-1640
    • Namdjou, D.J.1
  • 25
    • 0029741316 scopus 로고    scopus 로고
    • Functional relationships of the genetic locus encoding the glycosyltransferase enzymes involved in expression of the lacto-N-neotetoraose terminal lipopolysaccharide structure in Neisseria meningitides
    • Wakarchuk, W. W., Martin, A., Jennings, M. P., Moxon, E. R. & Richards, J. C. Functional relationships of the genetic locus encoding the glycosyltransferase enzymes involved in expression of the lacto-N-neotetoraose terminal lipopolysaccharide structure in Neisseria meningitides. J Biol Chem 271, 19166-19173 (1996).
    • (1996) J Biol Chem , vol.271 , pp. 19166-19173
    • Wakarchuk, W.W.1    Martin, A.2    Jennings, M.P.3    Moxon, E.R.4    Richards, J.C.5
  • 26
    • 33644656768 scopus 로고    scopus 로고
    • Pharmacodynamic evaluation of the intracellular activities of antibiotics against Staphylococcusaureus in a model of THP-1 macrophages
    • Barcia-Macay, M., Seral, C., Mingeot-Leclercq, M. P., Tulkens, P. M. & Van Bambeke, F. Pharmacodynamic evaluation of the intracellular activities of antibiotics against Staphylococcusaureus in a model of THP-1 macrophages. Antimicrob. Agents Chemother. 50, 841-851 (2006).
    • (2006) Antimicrob. Agents Chemother. , vol.50 , pp. 841-851
    • Barcia-Macay, M.1    Seral, C.2    Mingeot-Leclercq, M.P.3    Tulkens, P.M.4    Van Bambeke, F.5


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