Kodaistatin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01552 |
| CAS | |
| Molecular Weight | 646.64 |
| Molecular Formula | C35H34O12 |
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Description
Kodaistatin B is originally isolated from Asperrgilus terreus Thom DSM 11237. It inhibits the glucose-6-phosphotransferase T1 (G-6-P-T1) with the IC50 of 130 nmol/L.
Specification
| Synonyms | Kodaistatin B |
| IUPAC Name | (5Z)-3-[2-[5-acetyl-2-[(3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-dihydroxy-3-oxocyclopenten-1-yl]-4,5-dihydroxyphenyl]-5-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxyfuran-2-one |
| Canonical SMILES | CCC(C)C=C(C)C=CC(=O)CC1=C(C(C(C1=O)O)(C(=O)C)O)C2=CC(=C(C=C2C3=C(C(=CC4=CC(=C(C=C4)O)O)OC3=O)O)O)O |
| InChI | InChI=1S/C35H34O12/c1-5-16(2)10-17(3)6-8-20(37)13-23-30(35(46,18(4)36)33(44)31(23)42)22-15-27(41)26(40)14-21(22)29-32(43)28(47-34(29)45)12-19-7-9-24(38)25(39)11-19/h6-12,14-16,33,38-41,43-44,46H,5,13H2,1-4H3/b8-6+,17-10+,28-12- |
| InChI Key | KFMTUTLQSGURRM-MARNYXESSA-N |
Properties
| Appearance | Yellow Solid |
Reference Reading
1. Kodaistatins, novel inhibitors of glucose-6-phosphate translocase T1 from Aspergillus terreus thom DSM 11247. Isolation and structural elucidation
L Vértesy, H J Burger, J Kenja, M Knauf, H Kogler, E F Paulus, N V Ramakrishna, K H Swamy, E K Vijayakumar, P Hammann J Antibiot (Tokyo). 2000 Jul;53(7):677-86. doi: 10.7164/antibiotics.53.677.
Two novel compounds, kodaistatin A, C35H34O11, molecular weight 630, and kodaistatin C, C35H34O12, molecular weight 646, have been isolated from cultures of Aspergillus terreus Thom DSM 11247 by solid-phase extraction, size-exclusion chromatography, and various preparative HPLC steps. The use of a range of 2D NMR measurements, in particular 13C-13C correlation measurements, has led to the clarification of the structure of kodaistatin A. Kodaistatin C is a hydroxylated derivative of kodaistatin A. Both natural products contain hydroxylated aspulvinones and identical highly substituted polyketide units. An X-ray single crystal structure analysis of aspulvinon E demonstrated the z-configuration at the central double bond. The kodaistatins are effective inhibitors of the glucose-6-phosphate translocase component of the glucose-6-phosphatase system (EC 3.1.3.9), an enzyme system which is important for the control of blood glucose levels. The IC50 is 80 nM for kodaistatin A and 130 nM for kodaistatin C.
2. A New Approach to Models of the 4,5-Dihydroxycyclopentenone Core of the Kodaistatins A-D: Elucidation of the Diol Configuration in Kodaistatin A
David Peter, Reinhard Brückner Chemistry. 2017 Sep 7;23(50):12104-12109. doi: 10.1002/chem.201701185. Epub 2017 Jun 27.
The kodaistatins A-D are strongly anti-diabetic natural products from Aspergillus terreus that hold some promise of a novel diabetes cure. However, considerations of that kind face two drawbacks: 1) The kodaistatins A-D contain a heavily substituted pulvinone/cyclopentenone combination; 2) they are 1,2-diols, the 3D structures of which have not been assigned yet. However, we can exclude two of the four possible stereostructures. We conclude that kodaistatin A is a trans-, not a cis-diol from NMR comparisons with a pair of cis, trans-isomeric kodaistatin models, which we synthesized in 11 and 12 steps, respectively. The stereocenters of the diol moiety arose from stereocomplementary, highly diastereoselective aldol additions of a lithium enolate or the corresponding silyl ketene acetal. The cyclopentenone moieties stemmed from intramolecular aldol additions and ensuing dehydrations. The requisite enolates were obtained by the reduction of α-bromoketones with samarium diiodide.
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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 ╳
