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Brevicompanine B

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Brevicompanine B
Category Bioactive by-products
Catalog number BBF-04591
CAS 215121-47-4
Molecular Weight 367.48
Molecular Formula C22H29N3O2
Purity >99% by HPLC

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

A diketopiperazine-related metabolite produced by penicillium brevicompactum and aspergillus species. It has obvious plant growth regulation activity, but is devoid of antifungal or antimicrobial activity. It is active against Plasmodium falciparum.

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Synonyms (3R,5aS,10bR,11aS)-10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
Storage Store at -20°C
IUPAC Name (1S,4R,7S,9R)-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
Canonical SMILES CC(C)CC1C(=O)N2C(CC3(C2NC4=CC=CC=C43)C(C)(C)C=C)C(=O)N1
InChI InChI=1S/C22H29N3O2/c1-6-21(4,5)22-12-17-18(26)23-16(11-13(2)3)19(27)25(17)20(22)24-15-10-8-7-9-14(15)22/h6-10,13,16-17,20,24H,1,11-12H2,2-5H3,(H,23,26)/t16-,17+,20+,22-/m1/s1
InChI Key HAXPBJUEOMQIJN-HBCLNWRISA-N
Source Penicillium sp.
Appearance Amorphous Powder
Antibiotic Activity Spectrum Parasites
Boiling Point 576.8±50.0°C at 760 mmHg
Melting Point 79-82°C
Density 1.2±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water
1. Diketopiperazine alkaloids from a deep ocean sediment derived fungus Penicillium sp
Tianjiao Zhu, Qianqun Gu, Lin Du, Hyun Park, Xinying Yang, Xiang Xiao, Fengping Wang Chem Pharm Bull (Tokyo) . 2009 Aug;57(8):873-6. doi: 10.1248/cpb.57.873.
Five new diketopiperazine alkaloids, brevicompanines D-H (3-7), together with two known analogs, allo-brevicompanine B (1) and fructigenine B (2), were isolated from a deep ocean sediment derived fungus Penicillium sp. Their structures were established by spectroscopic methods including 2D NMR and chiral HPLC analysis. Compounds 4 and 7 inhibited lipopolysaccharide (LPS)-induced nitric oxide production in BV2 microglial cells.
2. Ir-catalyzed reverse prenylation of 3-substituted indoles: total synthesis of (+)-aszonalenin and (-)-brevicompanine B
Erick M Carreira, Jonathan Ruchti J Am Chem Soc . 2014 Dec 3;136(48):16756-9. doi: 10.1021/ja509893s.
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.

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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