Tryprostatin A
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| Category | Bioactive by-products |
| Catalog number | BBF-03425 |
| CAS | 171864-80-5 |
| Molecular Weight | 381.47 |
| Molecular Formula | C22H27N3O3 |
| Purity | 98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03425 | 1 mg | $629 | In stock |
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Add to cartDescription
Tryprostatin A is a natural compound isolated from Aspergillus fumigatus and arrests cell cycle progression at the G2/M phase.
Specification
| Synonyms | (3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione |
| Storage | Store at-20°C |
| IUPAC Name | (3S,8aS)-3-[[6-methoxy-2-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione |
| Canonical SMILES | CC(=CCC1=C(C2=C(N1)C=C(C=C2)OC)CC3C(=O)N4CCCC4C(=O)N3)C |
| InChI | InChI=1S/C22H27N3O3/c1-13(2)6-9-17-16(15-8-7-14(28-3)11-18(15)23-17)12-19-22(27)25-10-4-5-20(25)21(26)24-19/h6-8,11,19-20,23H,4-5,9-10,12H2,1-3H3,(H,24,26)/t19-,20-/m0/s1 |
| InChI Key | XNRPVPHNDQHWLJ-PMACEKPBSA-N |
Properties
| Appearance | Pale Yellow Crystalline Solid |
| Boiling Point | 666.43°C at 760 mmHg |
| Melting Point | 120-123°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in methanol, absolute ethanol, and DMSO. |
Reference Reading
1. Indole C6 Functionalization of Tryprostatin B Using Prenyltransferase CdpNPT
Eric D Gardner, Dustin A Dimas, Matthew C Finneran, Sara M Brown, Anthony W Burgett, Shanteri Singh Catalysts. 2020 Nov;10(11):1247. doi: 10.3390/catal10111247. Epub 2020 Oct 28.
Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II and tubulin polymerization. However, the inability to perform late-stage modification of the indole ring has limited the structure-activity relationship studies of this class of natural products. Herein, we describe an efficient chemoenzymatic approach for the late-stage modification of tryprostatin B using a cyclic dipeptide N-prenyltransferase (CdpNPT) from Aspergillus fumigatus, which generates novel analogs functionalized with allylic, benzylic, heterocyclic, and diene moieties. Notably, this biocatalytic functionalizational study revealed high selectivity for the indole C6 position. Seven of the 11 structurally characterized analogs were exclusively C6-alkylated, and the remaining four contained predominant C6-regioisomers. Of the 24 accepted substrates, 10 provided >50% conversion and eight provided 20-50% conversion, with the remaining six giving <20% conversion under standard conditions. This study demonstrates that prenyltransferase-based late-stage diversification enables direct access to previously inaccessible natural product analogs.
2. Synthesis of tryptophan-containing 2,5-diketopiperazines via sequential C-H activation: total syntheses of tryprostatin A, maremycins A and B
Xue-Song Yin, Wei-Yi Qi, Bing-Feng Shi Chem Sci. 2021 Sep 7;12(39):13137-13143. doi: 10.1039/d1sc02343h. eCollection 2021 Oct 13.
Indole 2,5-diketopiperazines (DKPs) are an important type of metabolic cyclic dipeptides containing a tryptophan (Trp) unit possessing a range of interesting biological activities. The intriguing structural features and divergent activities have stimulated tremendous efforts towards their efficient synthesis. Herein, we report the development of a unified strategy for the synthesis of three Trp-containing DKPs, namely tryprostatin A, and maremycins A and B, via a sequential C-H activation strategy. The key Trp skeletons were synthesized from the inexpensive, readily available alanine via a Pd(ii)-catalyzed β-methyl C(sp3)-H monoarylation. A subsequent C2-selective prenylation of the resulting 6-OMe-Trp by Pd/norbornene-promoted C-H activation led to the total synthesis of tryprostatin A in 12 linear steps from alanine with 25% overall yield. Meanwhile, total syntheses of maremycins A and B were successfully accomplished using a sequential Pd-catalyzed methylene C(sp3)-H methylation as the key step in 15 linear steps from alanine.
3. Engineered Production of Tryprostatins in E. coli through Reconstitution of a Partial ftm Biosynthetic Gene Cluster from Aspergillus sp
Gopitkumar R Shah, Shane R Wesener, Yi-Qiang Cheng Jacobs J Biotechnol Bioeng. 2015 Apr;2(1):009. Epub 2014 Dec 18.
Tryprostatin A and B are indole alkaloid-based fungal products that inhibit mammalian cell cycle at the G2/M phase. They are biosynthetic intermediates of fumitremorgins produced by a complex pathway involving a nonribosomal peptide synthetase (FtmA), a prenyltransferase (FtmB), a cytochrome P450 hydroxylase (FtmC), an O-methyltransferase (FtmD), and several additional enzymes. A partial fumitremorgin biosynthetic gene cluster (ftmABCD) from Aspergillus sp. was reconstituted in Escherichia coli BL21(DE3) cells, with or without the co-expression of an Sfp-type phosphopantetheinyltransferase gene (Cv_sfp) from Chromobacterium violaceum No. 968. Several recombinant E. coli strains produced tryprostatin B up to 106 mg/l or tryprostatin A up to 76 mg/l in the fermentation broth under aerobic condition, providing an effective way to prepare those pharmaceutically important natural products biologically.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
