Vancomycin : Cluster information

Compound

Entry name	Vancomycin
Moiety description	A: aglycone B: beta-hydroxytyrosine(Bht) C: L-3,5-dihydroxyphenylglycine(Dpg)
PKS Type	A: NRPS B: other C: TypeIII
Starter Unit	C: malonyl-CoA
Chain Length	C: 4
Sugar Unit	L-vancosamine-1,2-glucose
Classification	Glycopeptide(vancomycin-type)
Activity	Antibacterial
Composition	C₆₆H₇₅Cl₂N₉O₂₄

Original source

Organism	Amycolatopsis orientalis
Strain	ATCC 19795 (=NBRC 12806)
Contig	HE589771

PKS/NRPS Module

A	Vanco_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)
B	Vanco_00230 vpsD	1	tyrosine
C	Vanco_00320 dpgA	1

A	36..427

PCP	503..569

C	600..892

A	1058..1448

PCP	1523..1589

E	1623..2075

C	2088..2379

A	2560..2962

PCP	3044..3110

C	7..301

A	482..879

PCP	957..1023

E	1060..1488

C	1497..1788

A	1969..2363

PCP	2446..2512

E	2549..2994

C	3006..3297

A	3481..3870

PCP	3955..4021

C	15..313

A	496..891

PCP	974..1041

X	1055..1354

TE	1627..1844

A	43..435

PCP	516..583

CHS	56..370

Reference

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