Brevianamide F

Brevianamide F , also known as cyclo-(L-Trp-L-Pro), belongs to a class of naturally occurring 2,5-diketopiperazines.^[1] It is the simplest member and the biosynthetic precursor of a large family of biologically active prenylated tryptophan-proline 2,5-diketopiperazines that are produced by the fungi A. fumigatus^[2] and Aspergillus sp.^[3] It has been isolated from the bacterium Streptomyces sp. strain TN58 and shown to possess activity against the Gram-positive bacteria S. aureus and Micrococcus luteus.^[4] It has also been isolated from Bacillus cereus associated with the entomopathogenic nematode Rhabditis (Oscheius) sp. and shown to have antifungal activity against T. rubrum, C. neoformans, and C. albicans, better than amphotericin B.^[5] Although the proline 2,5-diketopiperazines are the most abundant and structurally diverse 2,5-diketopiperazines found in food, cyclo(L-Trp-L-Pro) has only been found as a minor 2,5-diketopiperazine (8.2 ppm) in autolyzed yeast extract.^[6] Initially, cyclo(L-Trp-L-Pro) and its DL, LD, and DD isomers showed potential for use in the treatment of cardiovascular dysfunction,^[7] but they were later shown to be hepatotoxic.^[8]

Quick facts Names, Identifiers ...

Brevianamide F

Names
Preferred IUPAC name (3S,8aS)-3-[(1H-Indol-3-yl)methyl]hexahydropyrido[1,2-a]pyrazine-1,4-dione
Other names Cyclo-(L-Trp-L-Pro)
Identifiers
CAS Number	38136-70-8
3D model (JSmol)	Interactive image
ChemSpider	157941
PubChem CID	181567
UNII	76XZ426FPP Y
CompTox Dashboard (EPA)	DTXSID10959075
InChI InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1 Key: RYFZBPVMVYTEKZ-KBPBESRZSA-N
SMILES [H][C@@]12CCCN1C(=O)[C@H](Cc1c[nH]c3ccccc13)NC2=O
Properties
Chemical formula	C16H17N3O2
Molar mass	283.331 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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