Scytalol C
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| Category | Others |
| Catalog number | BBF-02893 |
| CAS | 208183-22-6 |
| Molecular Weight | 320.34 |
| Molecular Formula | C17H20O6 |
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Description
It is produced by the strain of Scytalidium sp. 36-93.
Specification
| Synonyms | Naphtho[1,2-b]furan-5(4H)-one,2,3,3a,9btetrahydro-6-hydroxy-2,8-dimethoxy-4-(methoxymethylene)-2-methyl-, (2R,3aR,4E,9bR)-rel-(-)- |
| IUPAC Name | (2R,3aR,4E,9bR)-6-hydroxy-2,8-dimethoxy-4-(methoxymethylidene)-2-methyl-3a,9b-dihydro-3H-benzo[g][1]benzofuran-5-one |
| Canonical SMILES | CC1(CC2C(O1)C3=C(C(=CC(=C3)OC)O)C(=O)C2=COC)OC |
| InChI | InChI=1S/C17H20O6/c1-17(22-4)7-11-12(8-20-2)15(19)14-10(16(11)23-17)5-9(21-3)6-13(14)18/h5-6,8,11,16,18H,7H2,1-4H3/b12-8+/t11-,16+,17-/m1/s1 |
| InChI Key | YNQDIUITYOXMCO-GQTFHTRASA-N |
Properties
| Appearance | White Crystal |
| Melting Point | 169-171°C |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. New compounds from Japanese oak wilt disease-associated fungus Raffaelea quercivora
Tomoki Nakamura, Unang Supratman, Desi Harneti, Rani Maharani, Takuya Koseki, Yoshihito Shiono Nat Prod Res. 2021 Dec;35(23):5304-5310. doi: 10.1080/14786419.2020.1753054. Epub 2020 Apr 14.
Two new compounds, a new lactone, quercilactone A (1), and (17R)-hydroxynafuredin (5), as well as five known compounds, scytalone (2), 3S,4R-hydoxy-scytalone (3), nafuredin (4), (+)-(3R,5R)-3-hydroxy-5-decanolide (6) and 3-ethyl-4-hydroxy-6-methyl-2H-pyran-2-one (7), were isolated from Raffaelea quercivora, a fungus that causes Japanese oak wilt disease. The structures of these compounds were determined by 1D and 2D NMR spectroscopic analyses. The absolute configuration at C-17 of 5 was determined to be R by the modified Mosher's method. Compounds 1, 2, and 7 exhibited weak phytotoxic activity in lettuce seedlings at a concentration of 100 μg mL-1.
2. A scytalone dehydratase gene from Ophiostoma floccosum restores the melanization and pathogenicity phenotypes of a melanin-deficient Colletotrichum lagenarium mutant
H L Wang, S H Kim, C Breuil Mol Genet Genomics. 2001 Sep;266(1):126-32. doi: 10.1007/s004380100534.
Scytalone dehydratase is involved in the production of fungal dihydroxynaphthalene (DHN) melanin. We have isolated and characterized OSD1, a gene encoding scytalone dehydratase from the sap-staining fungus Ophiostoma floccosum by PCR-based cloning. Sequence analysis suggests that the OSD1 gene encodes a protein of 216 amino acids with a molecular weight of 24.2 kDa that shows 51-70% sequence identity to other scytalone dehydratases. The cloned OSD1 contains two introns of 76 bp and 63 bp in length, and is the longest scytalone dehydratase gene sequence so far reported. Transformation of a DHN melanin-deficient, non-pathogenic, mutant of Colletotrichum lagenarium with the OSD1 gene restored melanin production and pathogenicity. The ability of the mutant to produce the OSD1 gene product was confirmed by RT-PCR analysis. These data show that the cloned OSD1 gene product can function in the DHN melanin biosynthetic pathway in C. lagenarium.
3. Crystallization of scytalone dehydratase F162A mutant in the unligated state and a preliminary X-ray diffraction study at 37 K
Takayuki Motoyama, Masayoshi Nakasako, Isamu Yamaguchi Acta Crystallogr D Biol Crystallogr. 2002 Jan;58(Pt 1):148-50. doi: 10.1107/s0907444901017371. Epub 2001 Dec 21.
Scytalone dehydratase variant F162A, in which Phe162 in the C-terminal region was replaced with alanine, was crystallized with polyethylene glycol 4000. Because the crystal was radiation-sensitive, the diffraction data were collected at cryogenic temperatures. The crystal belonged to monoclinic space group P2(1), with unit-cell parameters a = 72.64, b = 61.30, c = 72.62 A, beta = 120.02 degrees at 37 K. The calculated V(M) value was acceptable when a trimer of the mutant enzyme occupied a crystallographic asymmetric unit. The resolution limit was extended to 1.45 A at BL41XU of SPring-8 at 37 K.
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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 ╳
