Defucogilvocarcin V
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| Category | Antibiotics |
| Catalog number | BBF-00798 |
| CAS | 80155-95-9 |
| Molecular Weight | 348.35 |
| Molecular Formula | C21H16O5 |
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Description
Defucogilvocarcin V is a gilvocarcin antibiotic produced by Streptomyces arenas 2046. Activity against gram-positive bacteria.
Specification
| Synonyms | 6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 8-ethenyl-1-hydroxy-10,12-dimethoxy-; Gilvocarcin V aglycone |
| IUPAC Name | 8-ethenyl-1-hydroxy-10,12-dimethoxynaphtho[1,2-c]isochromen-6-one |
| Canonical SMILES | COC1=CC(=CC2=C1C3=CC(=C4C(=C3OC2=O)C=CC=C4O)OC)C=C |
| InChI | InChI=1S/C21H16O5/c1-4-11-8-14-18(16(9-11)24-2)13-10-17(25-3)19-12(6-5-7-15(19)22)20(13)26-21(14)23/h4-10,22H,1H2,2-3H3 |
| InChI Key | CZOCDNQYMADMLK-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystalline Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 620.7°C at 760 mmHg |
| Melting Point | 253-257°C |
| Density | 1.339 g/cm3 |
Reference Reading
1. Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity
Tao Liu, Madan K Kharel, Lili Zhu, Samuel A Bright, Cynthia Mattingly, Val R Adams, Jürgen Rohr Chembiochem. 2009 Jan 26;10(2):278-86. doi: 10.1002/cbic.200800348.
Four new analogues of the gilvocarcin-type aryl-C-glycoside antitumor compounds, namely 4'-hydroxy gilvocarcin V (4'-OH-GV), 4'-hydroxy gilvocarcin M, 4'-hydroxy gilvocarcin E and 12-demethyl-defucogilvocarcin V, were produced through inactivation of the gilU gene. The 4'-OH-analogues showed improved activity against lung cancer cell lines as compared to their parent compounds without 4'-OH group (gilvocarcins V and E). The structures of the sugar-containing new mutant products indicate that the enzyme GilU acts as an unusual ketoreductase involved in the biosynthesis of the C-glycosidically linked deoxysugar moiety of the gilvocarcins. The structures of the new gilvocarcins indicate substrate flexibility of the post-polyketide synthase modifying enzymes, particularly the C-glycosyltransferase and the enzyme responsible for the sugar ring contraction. The results also shed light into biosynthetic sequence of events in the late steps of biosynthetic pathway of gilvocarcin V.
2. 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
Clint A James, Victor Snieckus J Org Chem. 2009 Jun 5;74(11):4080-93. doi: 10.1021/jo9001454.
A key directed remote metalation (DreM)-carbamoyl migration strategy was applied in an efficient synthesis of the naturally occurring 6H-naphtho[1,2-b]benzopyran-6-one defucogilvocarcin V (1a, Scheme 11). The required biarylcarbamate 33d was best prepared by a high yielding Suzuki coupling reaction of 31a with the differentially protected trioxygenated naphthalene coupling partner 32d which was synthesized using a selective acylation of a juglone derivative. In the late stages of the synthesis, the triflate 39 served as the common intermediate to install the required C-8 vinyl group of 1a (Stille coupling) as well as the required substituents for the preparation of defucogilvocarcins M (1b) and E (1c). A variety of protecting group strategies were investigated and provided insight into which groups are preferred for the DreM-carbamoyl migration process. The strategic lessons learned from this total synthesis were applied in the successful total synthesis of the structurally similar natural product arnottin I (2).
3. An inverse electron demand Diels-Alder-based total synthesis of defucogilvocarcin V and some C-8 analogues
Penchal Reddy Nandaluru, Graham J Bodwell J Org Chem. 2012 Sep 21;77(18):8028-37. doi: 10.1021/jo3012682. Epub 2012 Sep 4.
A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
