Mniopetal A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01949 |
| CAS | 158760-98-6 |
| Molecular Weight | 508.60 |
| Molecular Formula | C27H40O9 |
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Description
Mniopetal A is a reverse transcriptase inhibitor produced by Mniopetalum sp. 87256.
Specification
| Synonyms | 2-(Acetyloxy)decanoic acid, 4-formyl-3,3a,6,6a,7,8,9,10-octahydro-3,10-dihydroxy-7,7-dimethyl-1-oxo-1H-naptho(1,8-c)furan-yl ester |
| IUPAC Name | [(3S,6aS,9S,10R,10aR)-4-formyl-3,10-dihydroxy-7,7-dimethyl-1-oxo-3a,6,6a,8,9,10-hexahydro-3H-benzo[d][2]benzofuran-9-yl] 2-acetyloxydecanoate |
| Canonical SMILES | CCCCCCCCC(C(=O)OC1CC(C2CC=C(C3C2(C1O)C(=O)OC3O)C=O)(C)C)OC(=O)C |
| InChI | InChI=1S/C27H40O9/c1-5-6-7-8-9-10-11-18(34-16(2)29)23(31)35-19-14-26(3,4)20-13-12-17(15-28)21-24(32)36-25(33)27(20,21)22(19)30/h12,15,18-22,24,30,32H,5-11,13-14H2,1-4H3/t18?,19-,20-,21?,22-,24-,27+/m0/s1 |
| InChI Key | AXAFCVAELSOPHP-BMILKMJHSA-N |
Properties
| Appearance | Colorless Oil |
| Boiling Point | 669.6±55.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid
Y Suzuki, R Nishimaki, M Ishikawa, T Murata, K I Takao, K I Tadano J Org Chem. 2000 Dec 15;65(25):8595-607. doi: 10.1021/jo001004p.
We have achieved the total synthesis of (-)-mniopetal E, a drimane sesquiterpenoid which inhibits the reverse transcriptase of human immunodeficiency virus (HIV)-1. Our enantiospecific total synthesis of this target molecule in naturally occurring form commenced with a known 2,3-anhydro-D-arabinitol derivative, which was prepared using the Sharpless asymmetric epoxidation strategy. The key steps of our total synthesis were as follows: (1) a combination of highly stereocontrolled inter- and intramolecular Horner-Emmons carbon elongations for construction of a butenolide tethering a 1,2,4, 9-functionalized nona-5,7-diene moiety at the beta-carbon, (2) stereoselective thermal intramolecular Diels-Alder reaction of the thus-formed trienic compound, providing preferentially an endo-cycloadduct with the desired pi-facial selection, and (3) efficient transformation of the gamma-lactone moiety in the major cycloadduct to the gamma-hydroxy-gamma-lactone part in mniopetal E. Our total synthesis of (-)-mniopetal E established the unsettled absolute stereochemistry of the antibiotic.
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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 ╳
