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Cluster information : Vancomycin


close this sectionCompound

Entry nameVancomycin
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-vancosamine-1,2-glucose
ClassificationGlycopeptide(vancomycin-type)
ActivityAntibacterial
CompositionC66H75Cl2N9O24
Vancomycin

close this sectionOriginal source

Organism
StrainATCC 19795 (=NBRC 12806)
Contig
Click on the icon to see Genetic map.

close this sectionPKS/NRPS Module

AVanco_00080
vpsA
1 leucine
2 beta-hydroxytyrosine(Bht)
3 asparagine
Vanco_00090
vpsB
4 L-4-hydroxyphenylglycine(Hpg)
5 L-4-hydroxyphenylglycine(Hpg)
6 beta-hydroxytyrosine(Bht)
Vanco_00100
vpsC
7 L-3,5-dihydroxyphenylglycine(Dpg)
BVanco_00230
vpsD
1 tyrosine
CVanco_00320
dpgA
1
A36..427
PCP503..569
C600..892
A1058..1448
PCP1523..1589
E1623..2075
C2088..2379
A2560..2962
PCP3044..3110
C7..301
A482..879
PCP957..1023
E1060..1488
C1497..1788
A1969..2363
PCP2446..2512
E2549..2994
C3006..3297
A3481..3870
PCP3955..4021
C15..313
A496..891
PCP974..1041
X1055..1354
TE1627..1844
A43..435
PCP516..583
CHS56..370

close this sectionReference

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
Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides.
Losey HC, Jiang J, Biggins JB, Oberthur M, Ye XY, Dong SD, Kahne D, Thorson JS, Walsh CT
[PMID: 12498883]Chem Biol. 9 (2002) 1305-14
Vancomycin assembly: nature's way.
Hubbard BK, Walsh CT
[PMID: 12596194]Angew Chem Int Ed Engl. 42 (2003) 730-65
Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: interactions with acceptor and nucleotide ligands.
Mulichak AM, Lu W, Losey HC, Walsh CT, Garavito RM
[PMID: 15122882]Biochemistry. 43 (2004) 5170-80
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
Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions.
Zhang C, Griffith BR, Fu Q, Albermann C, Fu X, Lee IK, Li L, Thorson JS
[PMID: 16946071]Science. 313 (2006) 1291-4
Chapter 18. Molecular genetic approaches to analyze glycopeptide biosynthesis.
Wohlleben W, Stegmann E, Sussmuth RD
[PMID: 19374994]Methods Enzymol. 458 (2009) 459-86
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
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
Glycopeptide antibiotic biosynthesis.
Yim G, Thaker MN, Koteva K, Wright G
[PMID: 24220108]J Antibiot (Tokyo). 67 (2014) 31-41
Bis-chlorination of a hexapeptide-PCP conjugate by the halogenase involved in vancomycin biosynthesis.
Schmartz PC, Zerbe K, Abou-Hadeed K, Robinson JA
[PMID: 24756572]Org Biomol Chem. 12 (2014) 5574-7
Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate.
Nakayama A, Okano A, Feng Y, Collins JC, Collins KC, Walsh CT, Boger DL
[PMID: 24954524]Org Lett. 16 (2014) 3572-5
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

close this sectionData download

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

 

 
GenBank format
135 KB

close this sectionHistory

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