Spirotryprostatin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Bioactive by-products |
| Catalog number | BBF-04375 |
| CAS | 182234-25-9 |
| Molecular Weight | 395.45 |
| Molecular Formula | C22H25N3O4 |
| Purity | 98.0% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04375 | 1 mg | $629 | In stock |
Online Inquiry
Add to cartDescription
Spirotryprostatin A is an indole alkaloid found in Aspergillus fumigatus fungus, which exhibits anti-mitotic activity.
Specification
| Synonyms | Spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole]-2',5,10(1'H)-trione, 1,5a,6,7,8,10a-hexahydro-6'-methoxy-3-(2-methyl-1-propenyl)-, (2S,3S,5aS,10aS)-; (2S,3S,5aS,10aS)-1,5a,6,7,8,10a-Hexahydro-6'-methoxy-3-(2-methyl-1-propen-1-yl)spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole]-2',5,10(1'H)-trione; (-)-Spirotryprostatin A; (3S,3'S,5'aS,10'aS)-6-Methoxy-3'-(2-methylprop-1-enyl)spiro[1H-indole-3,2'-3,5a,6,7,8,10a-hexahydro-1H-dipyrrolo[1,2-c:1',4'-f]pyrazine]-2,5',10'-trione |
| Storage | Store at 2-8°C |
| IUPAC Name | (3S,5S,6S,9S)-6'-methoxy-6-(2-methylprop-1-enyl)spiro[1,7-diazatricyclo[7.3.0.03,7]dodecane-5,3'-1H-indole]-2,2',8-trione |
| Canonical SMILES | CC(=CC1C2(CC3N1C(=O)C4CCCN4C3=O)C5=C(C=C(C=C5)OC)NC2=O)C |
| InChI | InChI=1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1 |
| InChI Key | MQJKGSIAJNXSCM-ORGXJRBJSA-N |
Properties
| Appearance | Powder |
| Boiling Point | 658.9±55.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Structural and Functional Analyses of a Spiro-Carbon-Forming, Highly Promiscuous Epoxidase from Fungal Natural Product Biosynthesis
Takuma Matsushita, Shinji Kishimoto, Kodai Hara, Hiroshi Hashimoto, Kenji Watanabe Biochemistry. 2020 Dec 29;59(51):4787-4792. doi: 10.1021/acs.biochem.0c00896. Epub 2020 Dec 17.
Biosynthesis of fungal nonribosomal peptides frequently involves redox enzymes such as flavin-containing monooxygenase (FMO) to introduce complexity into the core chemical structure. One such example is the formation of spiro-carbons catalyzed by various oxidases. Because many chemically complex spiro-carbon-bearing natural products exhibit useful biological activities, understanding the mechanism of spiro-carbon biosynthesis is of great interest. We previously identified FqzB, an FMO from the fumiquinazoline biosynthetic pathway responsible for epoxidation of fumiquinazoline F that crosstalks with the fumitremorgin biosynthetic pathway to form spirotryprostatin A via epoxidation of the precursor fumitremorgin C. What makes FqzB more interesting is its relaxed substrate specificity, where it can accept a range of other substrates, including tryprostatins A and B along with its original substrate fumiquinazoline F. Here, we characterized FqzB crystallographically and examined FqzB and its site-specific mutants kinetically to understand how this promiscuous epoxidase works. Furthermore, the mutagenesis studies as well as computational docking experiments between the FqzB crystal structure and its known substrates spirotryprostatin A and B, as well as fumitremorgin C and fumiquinazoline F, provided insight into potential modes of substrate recognition and the source of broad substrate tolerance exhibited by this epoxidase. This study serves as a foundation for further characterization and engineering of this redox enzyme, which has potential utility as a valuable catalyst with broad substrate tolerance and an ability to introduce chemical complexity into carbon frameworks for chemoenzymatic and biosynthetic applications.
2. Enantioselective Total Synthesis of Spirotryprostatin A
Tianfeng Peng, Teng Liu, Jingfeng Zhao, Jianwei Dong, Yuxiang Zhao, Yixiao Yang, Xin Yan, Wenlu Xu, Xianfu Shen J Org Chem. 2022 Dec 16;87(24):16743-16754. doi: 10.1021/acs.joc.2c02391. Epub 2022 Nov 29.
In this paper, we disclosed a novel enantioselective total synthesis of spirotryprostatin A (1) in 15 steps with a 7.4% total yield from commercially available 2-iodo-5-methoxyaniline and γ-butyrolactone. The key step features of this synthesis include the copper-catalyzed cascade reaction of o-iodoaniline derivatives with alkynone to introduce the quaternary carbon stereocenter and an aza-Michael tandem reaction to construct the spiro[pyrrolidine-3,3'-oxindole] moiety.
3. Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization
Yong-Kai Xi, Hongbin Zhang, Rui-Xi Li, Shi-Yuan Kang, Jin Li, Yan Li Chemistry. 2019 Feb 26;25(12):3005-3009. doi: 10.1002/chem.201806411. Epub 2019 Jan 29.
Cyclodipeptide 2,5-diketopiperazines (DKP) are privileged structural units present in drugs and natural alkaloids. This work reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic α-addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l-glutamic acid is highlighted by its application to the concise total syntheses of 6-methoxyspirotryprostatin B (the first total synthesis), spirotryprostatin A, and spirotryprostatin B.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
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 ╳
