Brevianamide F
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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


Price and Availability

Size Price Shipping out time Quantity
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 1850 2 Weeks
1g USD 2850 2 Weeks
2g USD 4150 2 Weeks
5g USD 6450 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-26. Prices are subject to change without notice.

Brevianamide F, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

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


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

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.