MedKoo Cat#: 406738 | Name: Brevianamide F
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Brevianamide F
Brevianamide F
CAS#38136-70-8

Theoretical Analysis

MedKoo Cat#: 406738

Name: Brevianamide F

CAS#: 38136-70-8

Chemical Formula: C16H17N3O2

Exact Mass: 283.1320

Molecular Weight: 283.33

Elemental Analysis: C, 67.83; H, 6.05; N, 14.83; O, 11.29

Price and Availability

Size Price Availability Quantity
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 1,850.00 2 Weeks
1g USD 2,850.00 2 Weeks
2g USD 4,150.00 2 Weeks
5g USD 6,450.00 2 Weeks
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Related CAS #
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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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 283.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.