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Glisoprenin A

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Glisoprenin A
Category Enzyme inhibitors
Catalog number BBF-01253
CAS 144376-62-5
Molecular Weight 703.14
Molecular Formula C45H82O5
Purity 95%

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
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
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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