WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406738
CAS#: 38136-70-8
Description: Brevianamide F , also known as cyclo-(L-Trp-L-Pro), belongs to a class of naturally occurring 2,5-diketopiperazines. 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.fumigates and Aspergillus sp. It has been isolated from the bacterium Streptomyces sp. strain TN58 and shown to possess activity against two Gram-positive bacteria, S.aureus and Micrococcus luteus, and 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
MedKoo Cat#: 406738
Name: Brevianamide F
CAS#: 38136-70-8
Chemical Formula: C16H17N3O2
Exact Mass: 283.132
Molecular Weight: 283.331
Elemental Analysis: C, 67.83; H, 6.05; N, 14.83; O, 11.29
Synonym: Brevianamide F
IUPAC/Chemical Name: (3S,8aS)-3-((1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
InChi Key: RYFZBPVMVYTEKZ-KBPBESRZSA-N
InChi Code: 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
SMILES Code: O=C(N[C@H]1CC2=CNC3=C2C=CC=C3)[C@@](CCC4)([H])N4C1=O
1: Wauters I, Goossens H, Delbeke E, Muylaert K, Roman BI, Van Hecke K, Van
Speybroeck V, Stevens CV. Beyond the Diketopiperazine Family with Alternatively
Bridged Brevianamide F Analogues. J Org Chem. 2015 Aug 21;80(16):8046-54. doi:
10.1021/acs.joc.5b01161. Epub 2015 Aug 3. PubMed PMID: 26193166.
2: Yin S, Yu X, Wang Q, Liu XQ, Li SM. Identification of a brevianamide F reverse
prenyltransferase BrePT from Aspergillus versicolor with a broad substrate
specificity towards tryptophan-containing cyclic dipeptides. Appl Microbiol
Biotechnol. 2013 Feb;97(4):1649-60. doi: 10.1007/s00253-012-4130-0. Epub 2012 Jun
3. PubMed PMID: 22660767.
3: Maiya S, Grundmann A, Li SM, Turner G. The fumitremorgin gene cluster of
Aspergillus fumigatus: identification of a gene encoding brevianamide F
synthetase. Chembiochem. 2006 Jul;7(7):1062-9. PubMed PMID: 16755625.
4: Grundmann A, Li SM. Overproduction, purification and characterization of
FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus.
Microbiology. 2005 Jul;151(Pt 7):2199-207. PubMed PMID: 16000710.