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MedKoo Cat#: 581289 | Name: Gilvocarcin V
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gilvocarcin V is a metabolite that displays potent antibacterial, antifungal and antiviral activity, from Actinomycete DO-38.

Chemical Structure

Gilvocarcin V
Gilvocarcin V
CAS#77879-90-4

Theoretical Analysis

MedKoo Cat#: 581289

Name: Gilvocarcin V

CAS#: 77879-90-4

Chemical Formula: C27H26O9

Exact Mass: 494.1577

Molecular Weight: 494.50

Elemental Analysis: C, 65.58; H, 5.30; O, 29.12

Price and Availability

Size Price Availability Quantity
100µg USD 285.00 2 Weeks
250µg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Gilvocarcin V; Gilvocarcina; Toromycin; DC-38-V; ANANDAMYCIN;
IUPAC/Chemical Name
1-hydroxy-10,12-dimethoxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)-8-vinyl-6H-dibenzo[c,h]chromen-6-one
InChi Key
MSXWAMODDZJPTG-QGZLGSDISA-N
InChi Code
1S/C27H26O9/c1-5-12-8-15-19(17(9-12)33-3)14-10-18(34-4)21-16(28)7-6-13(20(21)25(14)36-27(15)32)26-24(31)23(30)22(29)11(2)35-26/h5-11,22-24,26,28-31H,1H2,2-4H3/t11-,22+,23+,24-,26-/m1/s1
SMILES Code
c12c3c(c4c(cc(C=C)cc4OC)c(o3)=O)cc(c2c(O)ccc1[C@@H]1[C@@H]([C@H]([C@@H](O)[C@H](O1)C)O)O)OC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 494.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chen JM, Shepherd MD, Horn J, Leggas M, Rohr J. Enzymatic methylation and structure-activity-relationship studies on polycarcin V, a gilvocarcin-type antitumor agent. Chembiochem. 2014 Dec 15;15(18):2729-35. doi: 10.1002/cbic.201402426. Epub 2014 Nov 3. PubMed PMID: 25366963; PubMed Central PMCID: PMC4266428. 2: Cai X, Ng K, Panesar H, Moon SJ, Paredes M, Ishida K, Hertweck C, Minehan TG. Total synthesis of the antitumor natural product polycarcin V and evaluation of its DNA binding profile. Org Lett. 2014 Jun 6;16(11):2962-5. doi: 10.1021/ol501095w. Epub 2014 May 13. PubMed PMID: 24824354; PubMed Central PMCID: PMC4059221. 3: Tibrewal N, Downey TE, Van Lanen SG, Ul Sharif E, O'Doherty GA, Rohr J. Roles of the synergistic reductive O-methyltransferase GilM and of O-methyltransferase GilMT in the gilvocarcin biosynthetic pathway. J Am Chem Soc. 2012 Aug 1;134(30):12402-5. doi: 10.1021/ja305113d. Epub 2012 Jul 19. PubMed PMID: 22800463; PubMed Central PMCID: PMC3422024. 4: Pahari P, Kharel MK, Shepherd MD, van Lanen SG, Rohr J. Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis. Angew Chem Int Ed Engl. 2012 Jan 27;51(5):1216-20. doi: 10.1002/anie.201105882. Epub 2011 Dec 23. PubMed PMID: 22223167; PubMed Central PMCID: PMC3343456. 5: Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Shaaban KA, Rohr J. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat Prod Rep. 2012 Feb;29(2):264-325. doi: 10.1039/c1np00068c. Epub 2011 Dec 21. Review. PubMed PMID: 22186970. 6: Noinaj N, Bosserman MA, Schickli MA, Piszczek G, Kharel MK, Pahari P, Buchanan SK, Rohr J. The crystal structure and mechanism of an unusual oxidoreductase, GilR, involved in gilvocarcin V biosynthesis. J Biol Chem. 2011 Jul 1;286(26):23533-43. doi: 10.1074/jbc.M111.247833. Epub 2011 May 10. PubMed PMID: 21561854; PubMed Central PMCID: PMC3123116. 7: Shepherd MD, Liu T, Méndez C, Salas JA, Rohr J. Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties. Appl Environ Microbiol. 2011 Jan;77(2):435-41. doi: 10.1128/AEM.01774-10. Epub 2010 Nov 12. PubMed PMID: 21075894; PubMed Central PMCID: PMC3020532. 8: Shepherd MD, Kharel MK, Zhu LL, van Lanen SG, Rohr J. Delineating the earliest steps of gilvocarcin biosynthesis: role of GilP and GilQ in starter unit specificity. Org Biomol Chem. 2010 Sep 7;8(17):3851-6. doi: 10.1039/c0ob00036a. Epub 2010 Jul 8. PubMed PMID: 20617244. 9: Kharel MK, Nybo SE, Shepherd MD, Rohr J. Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters. Chembiochem. 2010 Mar 1;11(4):523-32. doi: 10.1002/cbic.200900673. PubMed PMID: 20140934; PubMed Central PMCID: PMC2879346. 10: James CA, Snieckus V. Combined directed remote metalation-transition metal catalyzed cross coupling strategies: the total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I. J Org Chem. 2009 Jun 5;74(11):4080-93. doi: 10.1021/jo9001454. PubMed PMID: 19441800. 11: Kharel MK, Pahari P, Lian H, Rohr J. GilR, an unusual lactone-forming enzyme involved in gilvocarcin biosynthesis. Chembiochem. 2009 May 25;10(8):1305-8. doi: 10.1002/cbic.200900130. Erratum in: Chembiochem. 2010 Jun 14;11(9):1161. PubMed PMID: 19388008; PubMed Central PMCID: PMC2879341. 12: Li YQ, Huang XS, Ishida K, Maier A, Kelter G, Jiang Y, Peschel G, Menzel KD, Li MG, Wen ML, Xu LH, Grabley S, Fiebig HH, Jiang CL, Hertweck C, Sattler I. Plasticity in gilvocarcin-type C-glycoside pathways: discovery and antitumoral evaluation of polycarcin V from Streptomyces polyformus. Org Biomol Chem. 2008 Oct 7;6(19):3601-5. doi: 10.1039/b808633h. Epub 2008 Jul 21. PubMed PMID: 19082162. 13: Liu T, Kharel MK, Zhu L, Bright SA, Mattingly C, Adams VR, Rohr J. Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity. Chembiochem. 2009 Jan 26;10(2):278-86. doi: 10.1002/cbic.200800348. PubMed PMID: 19067453; PubMed Central PMCID: PMC2680003. 14: Wang Q, Ding P, Perepelov AV, Xu Y, Wang Y, Knirel YA, Wang L, Feng L. Characterization of the dTDP-D-fucofuranose biosynthetic pathway in Escherichia coli O52. Mol Microbiol. 2008 Dec;70(6):1358-67. doi: 10.1111/j.1365-2958.2008.06449.x. Epub 2008 Oct 30. PubMed PMID: 19019146. 15: Kharel MK, Zhu L, Liu T, Rohr J. Multi-oxygenase complexes of the gilvocarcin and jadomycin biosyntheses. J Am Chem Soc. 2007 Apr 4;129(13):3780-1. Epub 2007 Mar 9. PubMed PMID: 17346045; PubMed Central PMCID: PMC2543133. 16: Liu T, Kharel MK, Fischer C, McCormick A, Rohr J. 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. Chembiochem. 2006 Jul;7(7):1070-7. PubMed PMID: 16795121; PubMed Central PMCID: PMC2879343. 17: Liu T, Fischer C, Beninga C, Rohr J. Oxidative rearrangement processes in the biosynthesis of gilvocarcin V. J Am Chem Soc. 2004 Oct 6;126(39):12262-3. PubMed PMID: 15453748. 18: Fischer C, Lipata F, Rohr J. The complete gene cluster of the antitumor agent gilvocarcin V and its implication for the biosynthesis of the gilvocarcins. J Am Chem Soc. 2003 Jul 2;125(26):7818-9. PubMed PMID: 12822997; PubMed Central PMCID: PMC4480634. 19: Matsumoto A, Hanawalt PC. Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts. Cancer Res. 2000 Jul 15;60(14):3921-6. PubMed PMID: 10919670. 20: Arce R, Oyola R, Alegría AE. The photobiological differences of gilvocarcins V and M are not related to their transient intermediates and triplet yields. Photochem Photobiol. 1998 Jul;68(1):25-31. PubMed PMID: 9679448.