Xenovulene A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02979 |
| CAS | |
| Molecular Weight | 358.47 |
| Molecular Formula | C22H30O4 |
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Description
It is produced by the strain of Acremonium strcturn. It has the effect of inhibiting the binding of Flunitrazepam to γ-aminobutyric acid-benzodiazapine with IC50 of 40 nmol/L.
Specification
| Synonyms | (2aR,5aR,11E,14aS,14bS,14cS)-4-Hydroxy-5a,9,9,12-tetramethyl-2a,5a,6,9,10,13,14,14a,14b,14c-decahydro-1,5-dioxacyclopenta[cd]cycloundeca[f]inden-3(2H)-one |
| IUPAC Name | (1S,2S,5E,9E,12R,17R,20S)-15-hydroxy-5,8,8,12-tetramethyl-13,19-dioxatetracyclo[12.5.1.02,12.017,20]icosa-5,9,14-trien-16-one |
| Canonical SMILES | CC1=CCC(C=CCC2(C(CC1)C3C4C(CO3)C(=O)C(=C4O2)O)C)(C)C |
| InChI | InChI=1S/C22H30O4/c1-13-6-7-15-19-16-14(12-25-19)17(23)18(24)20(16)26-22(15,4)10-5-9-21(2,3)11-8-13/h5,8-9,14-16,19,24H,6-7,10-12H2,1-4H3/b9-5+,13-8+/t14-,15-,16-,19-,22+/m0/s1 |
| InChI Key | WDFUVZRTUNQXHC-KVPIFFDFSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 487.1±45.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. A General Biomimetic Hetero-Diels-Alder Approach to the Core Skeletons of Xenovulene A and the Sterhirsutins A and B
Pei-Jun Li, Gerald Dräger, Andreas Kirschning Org Lett. 2019 Feb 15;21(4):998-1001. doi: 10.1021/acs.orglett.8b04003. Epub 2019 Jan 29.
A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.
2. Understanding and Engineering the Stereoselectivity of Humulene Synthase
Carsten Schotte, Peer Lukat, Adrian Deuschmann, Wulf Blankenfeldt, Russell J Cox Angew Chem Int Ed Engl. 2021 Sep 6;60(37):20308-20312. doi: 10.1002/anie.202106718. Epub 2021 Aug 11.
The non-canonical terpene cyclase AsR6 is responsible for the formation of 2E,6E,9E-humulene during the biosynthesis of the tropolone sesquiterpenoid (TS) xenovulene A. The structures of unliganded AsR6 and of AsR6 in complex with an in crystallo cyclized reaction product and thiolodiphosphate reveal a new farnesyl diphosphate binding motif that comprises a unique binuclear Mg2+ -cluster and an essential K289 residue that is conserved in all humulene synthases involved in TS formation. Structure-based site-directed mutagenesis of AsR6 and its homologue EupR3 identify a single residue, L285/M261, that controls the production of either 2E,6E,9E- or 2Z,6E,9E-humulene. A possible mechanism for the observed stereoselectivity was investigated using different isoprenoid precursors and results demonstrate that M261 has gatekeeping control over product formation.
3. Synthetic Biology Driven Biosynthesis of Unnatural Tropolone Sesquiterpenoids
Carsten Schotte, Lei Li, Daniel Wibberg, Jörn Kalinowski, Russell J Cox Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23870-23878. doi: 10.1002/anie.202009914. Epub 2020 Oct 26.
Tropolone sesquiterpenoids (TS) are an intriguing family of biologically active fungal meroterpenoids that arise through a unique intermolecular hetero Diels-Alder (hDA) reaction between humulene and tropolones. Here, we report on the combinatorial biosynthesis of a series of unprecedented analogs of the TS pycnidione 1 and xenovulene A 2. In a systematic synthetic biology driven approach, we recombined genes from three TS biosynthetic gene clusters (pycnidione 1, xenovulene A 2 and eupenifeldin 3) in the fungal host Aspergillus oryzae NSAR1. Rational design of the reconstituted pathways granted control over the number of hDA reactions taking place, the chemical nature of the fused polyketide moiety (tropolono- vs. monobenzo-pyranyl) and the degree of hydroxylation. Formation of unexpected monobenzopyranyl sesquiterpenoids was investigated using isotope-feeding studies to reveal a new and highly unusual oxidative ring contraction rearrangement.
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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 ╳
