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Cluster information : Balhimycin


close this sectionCompound

Entry nameBalhimycin
Moiety descriptionA: aglycone
B: beta-hydroxytyrosine(Bht)
C: L-3,5-dihydroxyphenylglycine(Dpg)
PKS TypeA: NRPS
B: other
C: TypeIII
Starter UnitC: malonyl-CoA
Chain LengthC: 4
Sugar UnitD-glucose
dehydrovancosamine
ClassificationGlycopeptide(vancomycin-type)
ActivityAntibacterial
CompositionC66H73Cl2N9O24
Balhimycin

close this sectionOriginal source

Organism
StrainDSM 5908
Contig
Click on the icon to see Genetic map.

close this sectionPKS/NRPS Module

ABalhi_00070
bpsA
1 leucine
2 beta-hydroxytyrosine(Bht)
3 asparagine
Balhi_00080
bpsB
4 L-4-hydroxyphenylglycine(Hpg)
5 L-4-hydroxyphenylglycine(Hpg)
6 beta-hydroxytyrosine(Bht)
Balhi_00090
bpsC
7 L-3,5-dihydroxyphenylglycine(Dpg)
BBalhi_00230
bpsD
1 tyrosine
CBalhi_00320
dpgA
1
A36..428
PCP504..570
C601..893
A1059..1449
PCP1524..1590
E1626..2077
C2089..2381
A2564..2970
PCP3052..3118
C7..301
A482..879
PCP957..1023
E1064..1500
C1509..1800
A1981..2375
PCP2458..2524
E2562..3011
C3023..3314
A3498..3887
PCP3974..4040
C15..310
A493..887
PCP969..1036
X1050..1349
TE1622..1836
A36..429
PCP510..577
CHS95..370

close this sectionReference

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
[PMID: 10390204]Antimicrob Agents Chemother. 43 (1999) 1565-73
The Biosynthesis of Vancomycin-Type Glycopeptide Antibiotics-New Insights into the Cyclization Steps This work was supported by the Deutsche Forschungsgemeinschaft (SFB 323). We thank M. Schierle, Dr. S. Stevanovic and Prof. H.-G. Rammensee for help with Edman degradation and J. Turner, Prof. B. List and Prof. D. Boger (La Jolla, USA) for discussions on the work.
Bischoff D, Pelzer S, Holtzel A, Nicholson GJ, Stockert S, Wohlleben W, Jung G, Sussmuth RD
[PMID: 11353482]Angew Chem Int Ed Engl. 40 (2001) 1693-1696
A polyketide synthase in glycopeptide biosynthesis: the biosynthesis of the non-proteinogenic amino acid (S)-3,5-dihydroxyphenylglycine.
Pfeifer V, Nicholson GJ, Ries J, Recktenwald J, Schefer AB, Shawky RM, Schroder J, Wohlleben W, Pelzer S
[PMID: 11495926]J Biol Chem. 276 (2001) 38370-7
Glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908: function of a halogenase and a haloperoxidase/perhydrolase.
Puk O, Huber P, Bischoff D, Recktenwald J, Jung G, Sussmuth RD, van Pee KH, Wohlleben W, Pelzer S
[PMID: 11880037]Chem Biol. 9 (2002) 225-35
Nonribosomal biosynthesis of vancomycin-type antibiotics: a heptapeptide backbone and eight peptide synthetase modules.
Recktenwald J, Shawky R, Puk O, Pfennig F, Keller U, Wohlleben W, Pelzer S
[PMID: 11932455]Microbiology. 148 (2002) 1105-18
The Biosynthesis of Vancomycin-Type Glycopeptide Antibiotics-The Order of the Cyclization Steps This work was supported by the Deutsche Forschungsgemeinschaft (SFB 323) and by a grant of the EU (MEGATOP, QLK3-1999-00650). R. D. S. gratefully acknowledges the support of a Feodor-Lynen Fellowship granted by the Alexander-von-Humboldt Stiftung. We thank Corina Bihlmaier and Volker Pfeifer for help with transformation and Southern hybridization, J. A. Moss (La Jolla (USA)) for critical comments on the manuscript and Prof. Dr. M. E. Maier and Prof. Dr. H.-P. Fiedler (Tubingen) for generous support.
Bischoff D, Pelzer S, Bister B, Nicholson GJ, Stockert S, Schirle M, Wohlleben W, Jung G, Sussmuth RD
[PMID: 12404385]Angew Chem Int Ed Engl. 40 (2001) 4688-4691
Vancomycin assembly: nature's way.
Hubbard BK, Walsh CT
[PMID: 12596194]Angew Chem Int Ed Engl. 42 (2003) 730-65
Structure of the TDP-epi-vancosaminyltransferase GtfA from the chloroeremomycin biosynthetic pathway.
Mulichak AM, Losey HC, Lu W, Wawrzak Z, Walsh CT, Garavito RM
[PMID: 12874381]Proc Natl Acad Sci U S A. 100 (2003) 9238-43
Mutasynthesis of glycopeptide antibiotics: variations of vancomycin's AB-ring amino acid 3,5-dihydroxyphenylglycine.
Weist S, Kittel C, Bischoff D, Bister B, Pfeifer V, Nicholson GJ, Wohlleben W, Sussmuth RD
[PMID: 15137740]J Am Chem Soc. 126 (2004) 5942-3
Biosynthesis of chloro-beta-hydroxytyrosine, a nonproteinogenic amino acid of the peptidic backbone of glycopeptide antibiotics.
Puk O, Bischoff D, Kittel C, Pelzer S, Weist S, Stegmann E, Sussmuth RD, Wohlleben W
[PMID: 15342578]J Bacteriol. 186 (2004) 6093-100
Precursor-directed biosynthesis for the generation of novel glycopetides.
Stegmann E, Bischoff D, Kittel C, Pelzer S, Puk O, Recktenwald J, Weist S, Sussmuth R, Wohlleben W
[PMID: 15645723]Ernst Schering Res Found Workshop. (2005) 215-32
The biosynthesis of vancomycin-type glycopeptide antibiotics--a model for oxidative side-chain cross-linking by oxygenases coupled to the action of peptide synthetases.
Bischoff D, Bister B, Bertazzo M, Pfeifer V, Stegmann E, Nicholson GJ, Keller S, Pelzer S, Wohlleben W, Sussmuth RD
[PMID: 15651041]Chembiochem. 6 (2005) 267-72
Comparative analysis and insights into the evolution of gene clusters for glycopeptide antibiotic biosynthesis.
Donadio S, Sosio M, Stegmann E, Weber T, Wohlleben W
[PMID: 16007453]Mol Genet Genomics. 274 (2005) 40-50
Genetic analysis of the balhimycin (vancomycin-type) oxygenase genes.
Stegmann E, Pelzer S, Bischoff D, Puk O, Stockert S, Butz D, Zerbe K, Robinson J, Sussmuth RD, Wohlleben W
[PMID: 16730832]J Biotechnol. 124 (2006) 640-53
The small MbtH-like protein encoded by an internal gene of the balhimycin biosynthetic gene cluster is not required for glycopeptide production.
Stegmann E, Rausch C, Stockert S, Burkert D, Wohlleben W
[PMID: 16907743]FEMS Microbiol Lett. 262 (2006) 85-92
Phylogenetic analysis of condensation domains in NRPS sheds light on their functional evolution.
Rausch C, Hoof I, Weber T, Wohlleben W, Huson DH
[PMID: 17506888]BMC Evol Biol. 7 (2007) 78
The border sequence of the balhimycin biosynthesis gene cluster from Amycolatopsis balhimycina contains bbr, encoding a StrR-like pathway-specific regulator.
Shawky RM, Puk O, Wietzorrek A, Pelzer S, Takano E, Wohlleben W, Stegmann E
[PMID: 17693715]J Mol Microbiol Biotechnol. 13 (2007) 76-88
The ABC transporter Tba of Amycolatopsis balhimycina is required for efficient export of the glycopeptide antibiotic balhimycin.
Menges R, Muth G, Wohlleben W, Stegmann E
[PMID: 17823795]Appl Microbiol Biotechnol. 77 (2007) 125-34
Phosphate-controlled regulator for the biosynthesis of the dalbavancin precursor A40926.
Alduina R, Lo Piccolo L, D'Alia D, Ferraro C, Gunnarsson N, Donadio S, Puglia AM
[PMID: 17873036]J Bacteriol. 189 (2007) 8120-9
The role of cep15 in the biosynthesis of chloroeremomycin: reactivation of an ancestral catalytic function.
Truman AW, Fan Q, Rottgen M, Stegmann E, Leadlay PF, Spencer JB
[PMID: 18482700]Chem Biol. 15 (2008) 476-84
Chapter 18. Molecular genetic approaches to analyze glycopeptide biosynthesis.
Wohlleben W, Stegmann E, Sussmuth RD
[PMID: 19374994]Methods Enzymol. 458 (2009) 459-86
The thioesterase Bhp is involved in the formation of beta-hydroxytyrosine during balhimycin biosynthesis in Amycolatopsis balhimycina.
Mulyani S, Egel E, Kittel C, Turkanovic S, Wohlleben W, Sussmuth RD, van Pee KH
[PMID: 19998400]Chembiochem. 11 (2010) 266-71
Genome mining in Amycolatopsis balhimycina for ferredoxins capable of supporting cytochrome P450 enzymes involved in glycopeptide antibiotic biosynthesis.
Geib N, Weber T, Wortz T, Zerbe K, Wohlleben W, Robinson JA
[PMID: 20337711]FEMS Microbiol Lett. 306 (2010) 45-53
Structural characterization of OxyD, a cytochrome P450 involved in beta-hydroxytyrosine formation in vancomycin biosynthesis.
Cryle MJ, Meinhart A, Schlichting I
[PMID: 20519494]J Biol Chem. 285 (2010) 24562-74
Increased glycopeptide production after overexpression of shikimate pathway genes being part of the balhimycin biosynthetic gene cluster.
Thykaer J, Nielsen J, Wohlleben W, Weber T, Gutknecht M, Lantz AE, Stegmann E
[PMID: 20570618]Metab Eng. 12 (2010) 455-61
Self-resistance and cell wall composition in the glycopeptide producer Amycolatopsis balhimycina.
Schaberle TF, Vollmer W, Frasch HJ, Huttel S, Kulik A, Rottgen M, von Thaler AK, Wohlleben W, Stegmann E
[PMID: 21690280]Antimicrob Agents Chemother. 55 (2011) 4283-9
Function of MbtH homologs in nonribosomal peptide biosynthesis and applications in secondary metabolite discovery.
Baltz RH
[PMID: 21826462]J Ind Microbiol Biotechnol. 38 (2011) 1747-60
Glycopeptide antibiotic biosynthesis.
Yim G, Thaker MN, Koteva K, Wright G
[PMID: 24220108]J Antibiot (Tokyo). 67 (2014) 31-41
Understanding the crucial interactions between Cytochrome P450s and non-ribosomal peptide synthetases during glycopeptide antibiotic biosynthesis.
Peschke M, Gonsior M, Sussmuth RD, Cryle MJ
[PMID: 27289043]Curr Opin Struct Biol. 41 (2016) 46-53
The VanRS Homologous Two-Component System VnlRSAb of the Glycopeptide Producer Amycolatopsis balhimycina Activates Transcription of the vanHAXSc Genes in Streptomyces coelicolor, but not in A. balhimycina.
Kilian R, Frasch HJ, Kulik A, Wohlleben W, Stegmann E
[PMID: 27420548]Microb Drug Resist. 22 (2016) 499-509

close this sectionData download

Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Balhimycin
Genomic nucleotide sequence
67 KB
Nucleotide sequences of the coding regions
67 KB
Translation of the coding sequences
24 KB
List of genes/ORFs
6 KB

 

 
GenBank format
134 KB

close this sectionHistory

  • 2016-12-27[Update]
  • 2015-02-12[Release]