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Cluster information : Chloroeremomycin


close this sectionCompound

Entry nameChloroeremomycin
SynonymA82846B
LY264826
Chloroorienticin A
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 UnitL-4-epivancosamine
L-4-epivancosamine-1,2-glucose
ClassificationGlycopeptide(vancomycin-type)
ActivityAntibacterial
CompositionC73H88Cl2N10O26
Chloroeremomycin

close this sectionOriginal source

Organism
StrainA82846UV37B
Contig
Click on the icon to see Genetic map.

close this sectionPKS/NRPS Module

AChlor_00030
cepA
1 leucine
2 beta-hydroxytyrosine(Bht)
3 asparagine
Chlor_00040
cepB
4 L-4-hydroxyphenylglycine(Hpg)
5 L-4-hydroxyphenylglycine(Hpg)
6 beta-hydroxytyrosine(Bht)
Chlor_00050
cepC
7 L-3,5-dihydroxyphenylglycine(Dpg)
BChlor_00200
cepK
1 tyrosine
CChlor_00280
dpgA
1
A38..427
PCP503..569
C602..891
A1058..1448
PCP1523..1589
E1631..2079
C2091..2382
A2567..2973
PCP3055..3121
C7..301
A482..879
PCP957..1023
E1063..1501
C1510..1801
A1982..2376
PCP2459..2525
E2563..3012
C3023..3314
A3499..3887
PCP3974..4040
C15..310
A493..889
PCP967..1038
X1052..1351
TE1624..1841
A36..428
PCP509..576
CHS98..370

close this sectionReference

Production of hybrid glycopeptide antibiotics in vitro and in Streptomyces toyocaensis.
Solenberg PJ, Matsushima P, Stack DR, Wilkie SC, Thompson RC, Baltz RH
[PMID: 9115410]Chem Biol. 4 (1997) 195-202
Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic.
van Wageningen AM, Kirkpatrick PN, Williams DH, Harris BR, Kershaw JK, Lennard NJ, Jones M, Jones SJ, Solenberg PJ
[PMID: 9545426]Chem Biol. 5 (1998) 155-62
Heterologous expression in Escherichia coli of the first module of the nonribosomal peptide synthetase for chloroeremomycin, a vancomycin-type glycopeptide antibiotic.
Trauger JW, Walsh CT
[PMID: 10716695]Proc Natl Acad Sci U S A. 97 (2000) 3112-7
Deoxysugars in glycopeptide antibiotics: enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis.
Chen H, Thomas MG, Hubbard BK, Losey HC, Walsh CT, Burkart MD
[PMID: 11035791]Proc Natl Acad Sci U S A. 97 (2000) 11942-7
Biosynthesis of L-p-hydroxyphenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics.
Hubbard BK, Thomas MG, Walsh CT
[PMID: 11137816]Chem Biol. 7 (2000) 931-42
Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides.
Losey HC, Peczuh MW, Chen Z, Eggert US, Dong SD, Pelczer I, Kahne D, Walsh CT
[PMID: 11294642]Biochemistry. 40 (2001) 4745-55
Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics.
Mulichak AM, Losey HC, Walsh CT, Garavito RM
[PMID: 11470430]Structure. 9 (2001) 547-57
Glycopeptide antibiotic biosynthesis: enzymatic assembly of the dedicated amino acid monomer (S)-3,5-dihydroxyphenylglycine.
Chen H, Tseng CC, Hubbard BK, Walsh CT
[PMID: 11752437]Proc Natl Acad Sci U S A. 98 (2001) 14901-6
Purification, crystallization and preliminary structural studies of dTDP-4-keto-6-deoxy-glucose-5-epimerase (EvaD) from Amycolatopsis orientalis, the fourth enzyme in the dTDP-L-epivancosamine biosynthetic pathway.
Merkel AB, Temple GK, Burkart MD, Losey HC, Beis K, Walsh CT, Naismith JH
[PMID: 12077451]Acta Crystallogr D Biol Crystallogr. 58 (2002) 1226-8
Biosynthesis of the vancomycin group of antibiotics: characterisation of a type III polyketide synthase in the pathway to (S)-3,5-dihydroxyphenylglycine.
Li TL, Choroba OW, Hong H, Williams DH, Spencer JB
[PMID: 12240210]Chem Commun (Camb). (2001) 2156-7
Characterisation of a hydroxymandelate oxidase involved in the biosynthesis of two unusual amino acids occurring in the vancomycin group of antibiotics.
Li TL, Choroba OW, Charles EH, Sandercock AM, Williams DH, Spencer JB
[PMID: 12240298]Chem Commun (Camb). (2001) 1752-3
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
Role of the active site cysteine of DpgA, a bacterial type III polyketide synthase.
Tseng CC, McLoughlin SM, Kelleher NL, Walsh CT
[PMID: 14744141]Biochemistry. 43 (2004) 970-80
Characterization of a regiospecific epivancosaminyl transferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin.
Lu W, Oberthur M, Leimkuhler C, Tao J, Kahne D, Walsh CT
[PMID: 15070728]Proc Natl Acad Sci U S A. 101 (2004) 4390-5
The position of a key tyrosine in dTDP-4-Keto-6-deoxy-D-glucose-5-epimerase (EvaD) alters the substrate profile for this RmlC-like enzyme.
Merkel AB, Major LL, Errey JC, Burkart MD, Field RA, Walsh CT, Naismith JH
[PMID: 15159413]J Biol Chem. 279 (2004) 32684-91
DpgC is a metal- and cofactor-free 3,5-dihydroxyphenylacetyl-CoA 1,2-dioxygenase in the vancomycin biosynthetic pathway.
Tseng CC, Vaillancourt FH, Bruner SD, Walsh CT
[PMID: 15380180]Chem Biol. 11 (2004) 1195-203
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
A systematic investigation of the synthetic utility of glycopeptide glycosyltransferases.
Oberthur M, Leimkuhler C, Kruger RG, Lu W, Walsh CT, Kahne D
[PMID: 16045364]J Am Chem Soc. 127 (2005) 10747-52
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
Two roads diverged: the structure of hydroxymandelate synthase from Amycolatopsis orientalis in complex with 4-hydroxymandelate.
Brownlee J, He P, Moran GR, Harrison DH
[PMID: 18215022]Biochemistry. 47 (2008) 2002-13
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
Structure and function of the glycopeptide N-methyltransferase MtfA, a tool for the biosynthesis of modified glycopeptide antibiotics.
Shi R, Lamb SS, Zakeri B, Proteau A, Cui Q, Sulea T, Matte A, Wright GD, Cygler M
[PMID: 19389626]Chem Biol. 16 (2009) 401-10
Chimeric glycosyltransferases for the generation of hybrid glycopeptides.
Truman AW, Dias MV, Wu S, Blundell TL, Huang F, Spencer JB
[PMID: 19549605]Chem Biol. 16 (2009) 676-85
Role of MbtH-like proteins in the adenylation of tyrosine during aminocoumarin and vancomycin biosynthesis.
Boll B, Taubitz T, Heide L
[PMID: 21890635]J Biol Chem. 286 (2011) 36281-90
Chain elongation and cyclization in type III PKS DpgA.
Wu HC, Li YS, Liu YC, Lyu SY, Wu CJ, Li TL
[PMID: 22492619]Chembiochem. 13 (2012) 862-71
Structure of EvaA: a paradigm for sugar 2,3-dehydratases.
Kubiak RL, Thoden JB, Holden HM
[PMID: 23473392]Biochemistry. 52 (2013) 2078-88
Glycopeptide antibiotic biosynthesis.
Yim G, Thaker MN, Koteva K, Wright G
[PMID: 24220108]J Antibiot (Tokyo). 67 (2014) 31-41

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Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Chloroeremomycin
Genomic nucleotide sequence
73 KB
Nucleotide sequences of the coding regions
22 KB
Translation of the coding sequences
14 KB
List of genes/ORFs
2 KB

 

 
GenBank format
145 KB
AJ223999
Genomic nucleotide sequence
35 KB
Nucleotide sequences of the coding regions
34 KB
Translation of the coding sequences
12 KB
List of genes/ORFs
1 KB

 

 

 
AJ223998
Genomic nucleotide sequence
38 KB
Nucleotide sequences of the coding regions
38 KB
Translation of the coding sequences
14 KB
List of genes/ORFs
4 KB

 

 

 

close this sectionHistory

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