메뉴 건너뛰기




Volumn 186, Issue 18, 2004, Pages 6093-6100

Biosynthesis of chloro-β-hydroxytyrosine, a nonproteinogenic amino acid of the peptidic backbone of glycopeptide antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTIBIOTIC AGENT; BALHIMYCIN; CHLORO BETA HYDROXYTYROSINE; CHLOROEREMOMYCIN; CYTOCHROME P450; CYTOCHROME P450 MONOOXYGENASE OXYD; GLYCOPEPTIDE; HYDROLASE; NONRIBOSOMAL PEPTIDE SYNTHETASE D; OXYGENASE; PEPTIDE SYNTHASE; PERHYDROLASE; PHENYLGLYCINE; RNA DIRECTED DNA POLYMERASE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

EID: 4444240578     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.186.18.6093-6100.2004     Document Type: Article
Times cited : (85)

References (38)
  • 1
    • 0027015144 scopus 로고
    • Positive selection vectors based on palindromic DNA sequences
    • Altenbuchner, J., P. Viell, and I. Pelletier. 1992. Positive selection vectors based on palindromic DNA sequences. Methods Enzymol. 216:457-466.
    • (1992) Methods Enzymol. , vol.216 , pp. 457-466
    • Altenbuchner, J.1    Viell, P.2    Pelletier, I.3
  • 3
    • 0030036676 scopus 로고    scopus 로고
    • Quantitative analysis of the metabolism of soluble cytoplasmic peptidoglycan precursors of glycopeptide-resistant enterococci
    • Arthur, M., F. Depardieu, P. Reynolds, and P. Courvalin. 1996. Quantitative analysis of the metabolism of soluble cytoplasmic peptidoglycan precursors of glycopeptide-resistant enterococci. Mol. Microbiol. 21:33-44.
    • (1996) Mol. Microbiol. , vol.21 , pp. 33-44
    • Arthur, M.1    Depardieu, F.2    Reynolds, P.3    Courvalin, P.4
  • 4
    • 0028942365 scopus 로고
    • Dimerization and membrane anchors in extracellular targeting of vancomycin group antibiotics
    • Beauregard, D. A., D. H. Williams, M. N. Gwynn, and D. J. C. Knowles. 1995. Dimerization and membrane anchors in extracellular targeting of vancomycin group antibiotics. Antimicrob. Agents Chemother. 39:781-785.
    • (1995) Antimicrob. Agents Chemother. , vol.39 , pp. 781-785
    • Beauregard, D.A.1    Williams, D.H.2    Gwynn, M.N.3    Knowles, D.J.C.4
  • 5
    • 0026645203 scopus 로고
    • Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp.
    • Bierman, M., R. Logan, K. O'Brien, E. T. Seno, R. N. Rao, and B. E. Schoner. 1992. Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116:43-49.
    • (1992) Gene , vol.116 , pp. 43-49
    • Bierman, M.1    Logan, R.2    O'Brien, K.3    Seno, E.T.4    Rao, R.N.5    Schoner, B.E.6
  • 7
    • 0000182975 scopus 로고
    • XL1-Blue, a high efficiency plasmid transforming recA Escherichia coli strain with beta galactosidase selection
    • Bullock, W. O., J. M. Fernandez, and J. M. Short. 1987. XL1-Blue, a high efficiency plasmid transforming recA Escherichia coli strain with beta galactosidase selection. Focus 5:376-378.
    • (1987) Focus , vol.5 , pp. 376-378
    • Bullock, W.O.1    Fernandez, J.M.2    Short, J.M.3
  • 8
    • 0027937508 scopus 로고
    • Balhimycin, a new glycopeptide antibiotic with an unusual hydrated 3-amino-4-oxoaldopyranose sugar moiety
    • Chatterjee, S., E. K. S. Vijayakumar, S. R. Nadkarni, M. V. Patel, J. Blumbach, and B. N. Ganguli. 1994. Balhimycin, a new glycopeptide antibiotic with an unusual hydrated 3-amino-4-oxoaldopyranose sugar moiety. J. Org. Chem. 59:3480-3484.
    • (1994) J. Org. Chem. , vol.59 , pp. 3480-3484
    • Chatterjee, S.1    Vijayakumar, E.K.S.2    Nadkarni, S.R.3    Patel, M.V.4    Blumbach, J.5    Ganguli, B.N.6
  • 9
    • 0035036477 scopus 로고    scopus 로고
    • Coumarin formation in novobiocin biosynthesis: β-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 Nov1
    • Chen, H., and C. T. Walsh. 2001. Coumarin formation in novobiocin biosynthesis: β-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 Nov1. Chem. Biol. 8:301-312.
    • (2001) Chem. Biol. , vol.8 , pp. 301-312
    • Chen, H.1    Walsh, C.T.2
  • 10
    • 0036008124 scopus 로고    scopus 로고
    • Formation of β-hydroxy histidine in the biosynthesis of nikkomycin antibiotics
    • Chen, H., B. K. Hubbard, S. E. O'Connor, and C. T. Walsh. 2002. Formation of β-hydroxy histidine in the biosynthesis of nikkomycin antibiotics. Chem. Biol. 9:103-112.
    • (2002) Chem. Biol. , vol.9 , pp. 103-112
    • Chen, H.1    Hubbard, B.K.2    O'Connor, S.E.3    Walsh, C.T.4
  • 11
    • 0034616852 scopus 로고    scopus 로고
    • Biosynthesis of the vancomycin group of antibiotics: Involvement of an unusual dioxygenase in the pathway to (S)-4-hydroxyphenylglycine
    • Choroba, O. W., D. H. Williams, and J. B. Spencer. 2000. Biosynthesis of the vancomycin group of antibiotics: involvement of an unusual dioxygenase in the pathway to (S)-4-hydroxyphenylglycine. J. Am. Chem. Soc. 122:5389-5390.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5389-5390
    • Choroba, O.W.1    Williams, D.H.2    Spencer, J.B.3
  • 12
    • 0027401261 scopus 로고
    • The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics
    • Gerhard, U., J. P. Mackay, R. A. Maplestone, and D. H. Williams. 1993. The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics. J. Am. Chem. Soc. 115:232-237.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 232-237
    • Gerhard, U.1    Mackay, J.P.2    Maplestone, R.A.3    Williams, D.H.4
  • 13
    • 0022346887 scopus 로고
    • The role of the chlorine substituents in the antibiotic vancomycin: Preparation and characterization of mono- and didechloro-vancomycin
    • Harris, C. M., R. Kannan, H. Kopecka, and T. M. Harris. 1985. The role of the chlorine substituents in the antibiotic vancomycin: preparation and characterization of mono- and didechloro-vancomycin. J. Am. Chem. Soc. 107:6652-6658.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6652-6658
    • Harris, C.M.1    Kannan, R.2    Kopecka, H.3    Harris, T.M.4
  • 15
    • 0034523992 scopus 로고    scopus 로고
    • Biosynthesis of L-p-hydroxy-phenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics
    • Hubbard, B. K., M. G. Thomas, and C. T. Walsh. 2000. Biosynthesis of L-p-hydroxy-phenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics. Chem. Biol. 7:931-942.
    • (2000) Chem. Biol. , vol.7 , pp. 931-942
    • Hubbard, B.K.1    Thomas, M.G.2    Walsh, C.T.3
  • 16
    • 0027936628 scopus 로고
    • Glycopeptide antibiotic activity and the possible role of dimerization: A model for biological signaling
    • Mackay, J. P., U. Gerhard, D. A. Beauregard, M. S. Westwell, M. S. Searle, and D. H. Williams. 1994. Glycopeptide antibiotic activity and the possible role of dimerization: a model for biological signaling. J. Am. Chem. Soc. 116:4581-4590.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4581-4590
    • Mackay, J.P.1    Gerhard, U.2    Beauregard, D.A.3    Westwell, M.S.4    Searle, M.S.5    Williams, D.H.6
  • 17
    • 9444278428 scopus 로고    scopus 로고
    • Modular peptide synthetases involved in nonribosomal peptide synthesis
    • Marahiel, M. A., T. Stachelhaus, and H. D. Mootz. 1997. Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 97:2651-2673.
    • (1997) Chem. Rev. , vol.97 , pp. 2651-2673
    • Marahiel, M.A.1    Stachelhaus, T.2    Mootz, H.D.3
  • 19
    • 0027177994 scopus 로고
    • Structure-activity relationships of vancomycin-type glycopeptide antibiotics
    • Nagarajan, S. R. 1993. Structure-activity relationships of vancomycin-type glycopeptide antibiotics. J. Antibiot. 46:1181-1195.
    • (1993) J. Antibiot. , vol.46 , pp. 1181-1195
    • Nagarajan, S.R.1
  • 21
    • 0343376474 scopus 로고    scopus 로고
    • Cloning and analysis of a peptide synthetase gene of the balhimycin producer Amycolatopsis mediterranei DSM5908 and development of a gene disruption/replacement system
    • Pelzer, S., W. Reichert, M. Huppert, D. Heckmann, and W. Wohlleben. 1997. Cloning and analysis of a peptide synthetase gene of the balhimycin producer Amycolatopsis mediterranei DSM5908 and development of a gene disruption/replacement system. J. Biotechnol. 56:115-128.
    • (1997) J. Biotechnol. , vol.56 , pp. 115-128
    • Pelzer, S.1    Reichert, W.2    Huppert, M.3    Heckmann, D.4    Wohlleben, W.5
  • 22
    • 0345643323 scopus 로고    scopus 로고
    • Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in the producing organism Amycolatopsis mediterranei DSM5908
    • Pelzer, S., R. Süßmuth, D. Heckmann, J. Recktenwald, P. Huber, G. Jung, and W. Wohlleben. 1999. Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in the producing organism Amycolatopsis mediterranei DSM5908. Antimicrob. Agents Chemother. 41:1565-1573.
    • (1999) Antimicrob. Agents Chemother. , vol.41 , pp. 1565-1573
    • Pelzer, S.1    Süßmuth, R.2    Heckmann, D.3    Recktenwald, J.4    Huber, P.5    Jung, G.6    Wohlleben, W.7
  • 23
  • 24
    • 0036953085 scopus 로고    scopus 로고
    • Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: New insights into the biosynthesis of aminocoumarin antibiotics
    • Pojer, F., S. M. Li, and L. Heide. 2002. Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Microbiology 148:3901-3911.
    • (2002) Microbiology , vol.148 , pp. 3901-3911
    • Pojer, F.1    Li, S.M.2    Heide, L.3
  • 27
    • 0036230911 scopus 로고    scopus 로고
    • Nonribosomal biosynthesis of vancomycin-type antibiotics: A heptapeptide backbone and eight peptide synthetase modules
    • Recktenwald, J., R. M. Shawky, O. Puk, F. Pfennig, U. Keller, W. Wohlleben, and S. Pelzer. 2002. Nonribosomal biosynthesis of vancomycin-type antibiotics: a heptapeptide backbone and eight peptide synthetase modules. Microbiology 148:1105-1118.
    • (2002) Microbiology , vol.148 , pp. 1105-1118
    • Recktenwald, J.1    Shawky, R.M.2    Puk, O.3    Pfennig, F.4    Keller, U.5    Wohlleben, W.6    Pelzer, S.7
  • 29
    • 0345097576 scopus 로고    scopus 로고
    • Learning from nature's drug factories: Nonribosomal synthesis of macrocyclic peptides
    • Sieber, S. A., and M. A. Marahiel. 2003. Learning from nature's drug factories: nonribosomal synthesis of macrocyclic peptides. J. Bacteriol. 185:7036-7043.
    • (2003) J. Bacteriol. , vol.185 , pp. 7036-7043
    • Sieber, S.A.1    Marahiel, M.A.2
  • 30
    • 0036008104 scopus 로고    scopus 로고
    • Expression analysis of the tylosin-biosynthetic gene cluster: Pivotal regulatory role of the tylQ product
    • Stratigopoulos, G., and E. Cundliffe. 2002. Expression analysis of the tylosin-biosynthetic gene cluster: pivotal regulatory role of the tylQ product. Chem. Biol. 9:71-78.
    • (2002) Chem. Biol. , vol.9 , pp. 71-78
    • Stratigopoulos, G.1    Cundliffe, E.2
  • 31
    • 0242491431 scopus 로고    scopus 로고
    • New advances in the biosynthesis of glycopeptide antibiotics of the vancomycin type from Amycolatopsis mediterranei
    • Süßmuth, R., S. Pelzer, G. Nicholson, T. Walk, W. Wohlleben, and G. Jung. 1999. New advances in the biosynthesis of glycopeptide antibiotics of the vancomycin type from Amycolatopsis mediterranei. Angew. Chem. 38:1976-1979.
    • (1999) Angew. Chem. , vol.38 , pp. 1976-1979
    • Süßmuth, R.1    Pelzer, S.2    Nicholson, G.3    Walk, T.4    Wohlleben, W.5    Jung, G.6
  • 32
    • 0020451893 scopus 로고
    • Physical analysis of antibiotic-resistance genes from Streptomyces and their use in vector construction
    • Thompson, C. J., T. Kieser, J. M. Ward, and D. A. Hopwood. 1982. Physical analysis of antibiotic-resistance genes from Streptomyces and their use in vector construction. Gene 20:51-62.
    • (1982) Gene , vol.20 , pp. 51-62
    • Thompson, C.J.1    Kieser, T.2    Ward, J.M.3    Hopwood, D.A.4
  • 33
    • 0035035061 scopus 로고    scopus 로고
    • Microbial biosynthesis of halometabolites
    • van Pée, K. H. 2001. Microbial biosynthesis of halometabolites. Arch. Microbiol. 175:250-258.
    • (2001) Arch. Microbiol. , vol.175 , pp. 250-258
    • Van Pée, K.H.1
  • 34
    • 0030053191 scopus 로고    scopus 로고
    • New 4-oxovancosamine-containing glycopeptide antibiotics from Amycolatopsis sp. Y-86,20122
    • Vértesy, L., H. W. Fehlhaber, H. Kogler, and M. Limbert. 1996. New 4-oxovancosamine-containing glycopeptide antibiotics from Amycolatopsis sp. Y-86,20122. J. Antibiot. 49:115-118.
    • (1996) J. Antibiot. , vol.49 , pp. 115-118
    • Vértesy, L.1    Fehlhaber, H.W.2    Kogler, H.3    Limbert, M.4
  • 36
    • 0242669191 scopus 로고    scopus 로고
    • Three new antibiotic producing species of the genus Amycolatopsis, Amycolatopsis balhimycina sp. nov., A. tolypomycina sp. nov., A. vancoresmycina sp. nov., and description of Amycolatopsis keratiniphila subsp. keratiniphila subsp. nov. and A. keratiniphila subsp. nogabecina subsp. nov.
    • Wink, J., R. M. Kroppenstedt, B. N. Ganguli, S. R. Nadkarni, P. Schumann, G. Seibert, and E. Stackebrandt. 2003. Three new antibiotic producing species of the genus Amycolatopsis, Amycolatopsis balhimycina sp. nov., A. tolypomycina sp. nov., A. vancoresmycina sp. nov., and description of Amycolatopsis keratiniphila subsp. keratiniphila subsp. nov. and A. keratiniphila subsp. nogabecina subsp. nov. Syst. Appl. Microbiol. 26:38-46.
    • (2003) Syst. Appl. Microbiol. , vol.26 , pp. 38-46
    • Wink, J.1    Kroppenstedt, R.M.2    Ganguli, B.N.3    Nadkarni, S.R.4    Schumann, P.5    Seibert, G.6    Stackebrandt, E.7
  • 37
    • 0002697711 scopus 로고
    • Glycopeptides: Classification, occurrence, and discovery
    • R. Nagarajan (ed.). Marcel Dekker Inc., New York, N.Y.
    • Yao, R. C., and L. W. Crandal. 1994. Glycopeptides: classification, occurrence, and discovery, p. 1-28. In R. Nagarajan (ed.), Glycopeptide antibiotics. Marcel Dekker Inc., New York, N.Y.
    • (1994) Glycopeptide Antibiotics , pp. 1-28
    • Yao, R.C.1    Crandal, L.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.