Brevianamide F | CAS#38136-70-8

Brevianamide F
new

featured

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

Chemical Structure

Brevianamide F

CAS# 38136-70-8

Instruction

Theoretical Analysis

MedKoo Cat#: 406738
Name: Brevianamide F
CAS#: 38136-70-8
Chemical Formula: C16H17N3O2
Exact Mass: 283.13
Molecular Weight: 283.331
Elemental Analysis: C, 67.83; H, 6.05; N, 14.83; O, 11.29

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 750
200mg	USD 1250
500mg	USD 1850
1g	USD 2850
2g	USD 4150
5g	USD 6450
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

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.

Your view history

Brevianamide F new featured