Gilvocarcin : Cluster information

Compound

Entry name	Gilvocarcin
PKS Type	TypeII
Starter Unit	Gilvocarcin M: acetyl-CoA Gilvocarcin V: propionyl-CoA
Chain Length	10
Sugar Unit	D-fucofuranose
Classification	Angucycline
Activity	Antibacterial Antitumor Antiviral
Composition	Gilvocarcin E: C₂₇H₂₈O₉ Gilvocarcin M: C₂₆H₂₆O₉ Gilvocarcin V: C₂₇H₂₆O₉

Original source

Organism	Streptomyces griseoflavus
Strain	Gö 3592
Contig	AY233211

PKS/NRPS Module

KS	3..372

CLF	4..351

ACP	6..79

AT	4..254

AT	23..331

Reference

The complete gene cluster of the antitumor agent gilvocarcin V and its implication for the biosynthesis of the gilvocarcins.: Fischer C, Lipata F, Rohr J
[PMID: 12822997]J Am Chem Soc. 125 (2003) 7818-9
Oxidative rearrangement processes in the biosynthesis of gilvocarcin V.: Liu T, Fischer C, Beninga C, Rohr J
[PMID: 15453748]J Am Chem Soc. 126 (2004) 12262-3
Inactivation of gilGT, encoding a C-glycosyltransferase, and gilOIII, encoding a P450 enzyme, allows the details of the late biosynthetic pathway to gilvocarcin V to be delineated.: Liu T, Kharel MK, Fischer C, McCormick A, Rohr J
[PMID: 16795121]Chembiochem. 7 (2006) 1070-7
Multi-oxygenase complexes of the gilvocarcin and jadomycin biosyntheses.: Kharel MK, Zhu L, Liu T, Rohr J
[PMID: 17346045]J Am Chem Soc. 129 (2007) 3780-1
Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity.: Liu T, Kharel MK, Zhu L, Bright SA, Mattingly C, Adams VR, Rohr J
[PMID: 19067453]Chembiochem. 10 (2009) 278-86
GilR, an unusual lactone-forming enzyme involved in gilvocarcin biosynthesis.: Kharel MK, Pahari P, Lian H, Rohr J
[PMID: 19388008]Chembiochem. 10 (2009) 1305-8
Enzymatic total synthesis of rabelomycin, an angucycline group antibiotic.: Kharel MK, Pahari P, Lian H, Rohr J
[PMID: 20486694]Org Lett. 12 (2010) 2814-7
Delineating the earliest steps of gilvocarcin biosynthesis: role of GilP and GilQ in starter unit specificity.: Shepherd MD, Kharel MK, Zhu LL, van Lanen SG, Rohr J
[PMID: 20617244]Org Biomol Chem. 8 (2010) 3851-6
Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties.: Shepherd MD, Liu T, Mendez C, Salas JA, Rohr J
[PMID: 21075894]Appl Environ Microbiol. 77 (2011) 435-41
The crystal structure and mechanism of an unusual oxidoreductase, GilR, involved in gilvocarcin V biosynthesis.: Noinaj N, Bosserman MA, Schickli MA, Piszczek G, Kharel MK, Pahari P, Buchanan SK, Rohr J
[PMID: 21561854]J Biol Chem. 286 (2011) 23533-43
Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis.: Pahari P, Kharel MK, Shepherd MD, van Lanen SG, Rohr J
[PMID: 22223167]Angew Chem Int Ed Engl. 51 (2012) 1216-20
Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology.: Kharel MK, Rohr J
[PMID: 22465094]Curr Opin Chem Biol. 16 (2012) 150-61
Roles of the synergistic reductive O-methyltransferase GilM and of O-methyltransferase GilMT in the gilvocarcin biosynthetic pathway.: Tibrewal N, Downey TE, Van Lanen SG, Ul Sharif E, O'Doherty GA, Rohr J
[PMID: 22800463]J Am Chem Soc. 134 (2012) 12402-5
Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis.: Tibrewal N, Pahari P, Wang G, Kharel MK, Morris C, Downey T, Hou Y, Bugni TS, Rohr J
[PMID: 23102024]J Am Chem Soc. 134 (2012) 18181-4