215121-47-4

Usage

Uses

Used in Pharmaceutical Industry:
Brevicompanine B is used as an antimalarial agent for its activity against the malaria parasite, Plasmodium falciparum, with an IC50 value of 35 mg/ml.
Used in Agriculture:
Brevicompanine B is used as a plant growth regulator for its ability to inhibit hypocotyl elongation in lettuce seedlings at a concentration of 100 mg/L and primary root growth in Arabidopsis seedlings at a concentration of 100 μM. It also disrupts the transcription of various genes involved in the regulation of plant circadian rhythm, making it a potential tool for improving crop yields and adjusting growth patterns.

Upstream product

• 5845-53-4 (R)-leucine methyl ester hydrochloride 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 358-72-5 dimethylallyl diphosphate 
• 56941-94-7 Cyclo(L-leucyl-L-tryptophyl) 
• 35661-60-0 N-(9-fluorenylmethoxycarbonyl)-D-leucine 
• 115-18-4 2-methyl-3-buten-2-ol 
• 861216-48-0 tert-butyl 2-methylbut-3-en-2-yl carbonate 
• 338391-59-6 methyl (2S)-2-[{(2S,3aS,8aR)-1,8-bis-t-butoxycarbonyl-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 338391-57-4 methyl (2R)-2-[{(2S,3aS,8aR)-1,8-bis-t-butoxycarbonyl-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 338391-60-9 methyl (2S)-2-[{(2S,3aS,8aR)-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 
• 159333-19-4 (2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-di-tert-butyl ester 
• 338391-58-5 methyl (2R)-2-[{(2S,3aS,8aR)-3a-(1,1-dimethylprop-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-2-yl}carbonylamino]-4-methylpentanoate 

Relevant academic research and scientific papers

Ir-catalyzed reverse prenylation of 3-substituted indoles: Total synthesis of (+)-aszonalenin and (-)-brevicompanine B

The selective reverse prenylation of 3-substituted-1H-indoles at C3 is described. The iridium-catalyzed reaction proceeds with high branched to linear selectivity (>20:1) for a variety of indoles. In addition, a diastereoselective reverse prenylation of tryptophan methyl ester is disclosed, and its synthetic utility is demonstrated in the synthesis of (+)-aszonalenin and (-)-brevicompanine B.

Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT

Six β-configured reversely C3-prenylated pyrrolo[2,3-b]indoles were successfully prepared by using a recombinant prenyltransferase from Neosartorya fischeri. For this purpose, the putative prenyltransferase gene NFIA-074280 (termed herewith cdpC3PT) was cloned into pQE60 and overexpressed in Escherichia coli. The overproduced His6-CdpC3PT was purified to near homogeneity and incubated with five cyclic tryptophan-containing dipeptides in the presence of dimethylallyl diphosphate (DMAPP). All of the substrates were accepted by CdpC3PT and converted to reversely C3-prenylated pyrrolo[2,3-b]indoles. Using cyclo-l-Trp-l-Trp as substrate, both mono- and diprenylated derivatives were obtained. The structures of the enzymatic products were confirmed by HR-ESI-MS, 1H- and 13C-NMR analyses as well as by long-range 1H-13C connectivities in heteronuclear multiple-bond correlation (HMBC) spectra after preparative isolation. 1H- 1H spatial correlations in nuclear overhauser effect spectroscopy (NOESY) were used for determination of absolute configuration. The KM values were determined at about 1.5 mM for DMAPP and in the range from 0.22 to 5.5 mM for cyclic dipeptides. The turnover number kcat were found in the range of 0.023 to 0.098 s-1 and specificity constants k cat/KM from 14.2 to 122.7 M-1 s-1. In contrast to the products of AnaPT bearing α-configured C3-dimethylallyl residues, the C3-prenyl moieties in the products of CdpC3PT have a β-configuration. Discovery and characterisation of CdpC3PT expand the usage of the chemoenzymatic approach for stereospecific synthesis of C3-prenylated derivatives.

Synthesis of brevicompanines, plant growth regulators

Brevicompanine A (1) and B (2) are plant growth regulators isolated from Penicillium brevicompactum. The synthesis of brevicompanine A (1) and B (2) was accomplished via a known intermediate.