Glisoprenin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01253 |
| CAS | 144376-62-5 |
| Molecular Weight | 703.14 |
| Molecular Formula | C45H82O5 |
| Purity | 95% |
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Description
It is produced by the strain of Gliocladium sp. FO-1513. It is a cholesterol acyltransferase (ACAT) inhibitor, and it can inhibit the formation of Appressorium on the hydrophobic surface of Magnaporthegrisea.
Specification
| Synonyms | (+)-GlisopreninA; FO 1513A; 2,6,10,14,34-Hexatriacontapentaene-1,19,23,27,31-pentol,3,7,11,15,19,23,27,31,35-nonamethyl- |
| IUPAC Name | (2E,6E,10E,14E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,34-pentaene-1,19,23,27,31-pentol |
| Canonical SMILES | CC(=CCCC(C)(CCCC(C)(CCCC(C)(CCCC(C)(CCCC(=CCCC(=CCCC(=CCCC(=CCO)C)C)C)C)O)O)O)O)C |
| InChI | InChI=1S/C45H82O5/c1-37(2)19-14-28-42(7,47)30-16-32-44(9,49)34-18-35-45(10,50)33-17-31-43(8,48)29-15-26-40(5)24-12-22-38(3)20-11-21-39(4)23-13-25-41(6)27-36-46/h19-20,23-24,27,46-50H,11-18,21-22,25-26,28-36H2,1-10H3/b38-20+,39-23+,40-24+,41-27+ |
| InChI Key | DVYSZUSSOIXHOF-VNEVDCACSA-N |
Properties
| Appearance | Colorless Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 779.1 °C at 760 mmHg |
| Density | 0.968 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Selectivity of microbial acyl-CoA: cholesterol acyltransferase inhibitors toward isozymes
Taichi Ohshiro, Lawrence L Rudel, Satoshi Omura, Hiroshi Tomoda J Antibiot (Tokyo). 2007 Jan;60(1):43-51. doi: 10.1038/ja.2007.6.
The selectivity of microbial inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT) toward the two isozymes, ACAT1 and ACAT2, was assessed in cell-based assays. Purpactin A (IC50 values of ACAT1 vs. IC50 values of ACAT2; 2.5 microM vs. 1.5 microM), terpendole C (10 microM vs. 10 microM), glisoprenin A (4.3 microM vs. 10 microM), spylidone (25 microM vs. 5.0 microM) and synthetic CL-283,546 (0.1 microM vs. 0.09 microM) inhibited ACAT1 and ACAT2 to similar extents. Beauveriolides I (0.6 microM vs. 20 microM) and III (0.9 microM vs. >20 microM) inhibited ACAT1 rather selectively, while pyripyropenes A (>80 microM vs. 0.07 microM), B (48 microM vs. 2.0 microM), C (32 microM vs. 0.36 microM) and D (38 microM vs. 1.5 microM) showed selective inhibition against ACAT2. In particular, pyripyropene A was found to be the most selective ACAT2 inhibitor with a selective index of more than 1,000.
2. Use of a chiral praseodymium shift reagent in predicting the complete stereostructure of glisoprenin A
Indranath Ghosh, Yoshito Kishi, Hiroshi Tomoda, Satoshi Omura Org Lett. 2004 Dec 9;6(25):4719-22. doi: 10.1021/ol048060n.
[structure: see text] The complete stereostructure of glisoprenin A has been predicted via analysis of the 13C NMR behaviors in the presence of (R)- and (S)-Pr(tfc)3.
3. Validation of lanthanide chiral shift reagents for determination of absolute configuration: total synthesis of glisoprenin A
Christopher M Adams, Indranath Ghosh, Yoshito Kishi Org Lett. 2004 Dec 9;6(25):4723-6. doi: 10.1021/ol048059o.
[structure: see text] The complete stereostructure of the natural product (+)-glisoprenin A had been predicted via a novel application of chiral lanthanide shift reagents. Confirmation of the predicted stereostructure of (+)-glisoprenin A and validation of the chiral lanthanide shift approach have now been achieved through total synthesis.
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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 ╳
