3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
- Product Name
- 3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
- CAS No.
- 170713-71-0
- Chemical Name
- 3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone
- Synonyms
- Aureusimine B;Aureusimine B, 10 mM in DMSO;6-BENZYL-3-ISOPROPYLPYRAZIN-2-ONE;6-benzyl-3-isopropylpyrazin-2(1H)-one;3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone;2(1H)-Pyrazinone, 3-(1-methylethyl)-6-(phenylmethyl)-
- CBNumber
- CB12682115
- Molecular Formula
- C14H16N2O
- Formula Weight
- 228.28964
- MOL File
- 170713-71-0.mol
3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone Property
- Melting point:
- 117-118 °C
- Density
- 1.10±0.1 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 11.65±0.60(Predicted)
- color
- Off-White to Light Grey
N-Bromosuccinimide Price
- Product number
- 18752
- Product name
- Aureusimine B
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $214
- Updated
- 2024/03/01
- Product number
- 18752
- Product name
- Aureusimine B
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $957
- Updated
- 2024/03/01
- Product number
- A794570
- Product name
- AureusimineB
- Packaging
- 5mg
- Price
- $185
- Updated
- 2021/12/16
- Product number
- 7138CR
- Product name
- 6-Benzyl-3-isopropyl-2(1H)-pyrazinone
- Packaging
- 5mg
- Price
- $1163
- Updated
- 2021/12/16
- Product number
- CM334858
- Product name
- 6-Benzyl-3-isopropylpyrazin-2(1H)-one
- Purity
- 95%+
- Packaging
- 1g
- Price
- $561
- Updated
- 2021/12/16
3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone Chemical Properties,Usage,Production
Description
Aureusimine B, also known as phevalin, is a natural pyrazinone produced by certain fungi and by Staphylococcus spp., including S. aureus. Its synthesis appears to be initiated by a conserved nonribosomal peptide synthetase that creates a dipeptide (phenylalanine-valine) aldehyde, which then undergoes cyclization and oxidation. Aureusimine B inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 μM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression.
Uses
Aureusimine B (phevalin) is a small molecular weight monoketopiperazine formed non-ribosomally by the fusion of phenylalanine and valine. Aureusimine B was isolated from S. aureus in 2010 as one of a pair of related metabolites, controversially identified as virulence factors in the pathology of Golden Staph. Aureusimine B is also an inhibitor of the protease, calpain.
Uses
Aureusimine B is a novel small molecule isolated from S. aureus as one of a pair of related metabolites controversially identified as virulence factors in the pathology of Golden Staph. Aureusimine B has also been reported as an inhibitor of the protease, calpain.
Definition
ChEBI: Phevalin is a member of the class of pyrazinones that is pyrazin-2(1H)-one substituted by an isopropyl and benzyl groups at position 3 and 6, respectively. It is a natural product found in Staphylococcus aureus that inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 muM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression. It has a role as a bacterial metabolite and a calpain inhibitor. It is a member of benzenes and a pyrazinone.
References
[1] M E ALVAREZ. Phevalin, a new calpain inhibitor, from a Streptomyces sp.[J]. Journal of Antibiotics, 1995, 48 10: 1165-1167. DOI: 10.7164/antibiotics.48.1165
[2] MICHAEL ZIMMERMANN Michael A F. A family of pyrazinone natural products from a conserved nonribosomal peptide synthetase in Staphylococcus aureus.[J]. Chemistry & biology, 2010: 925-930. DOI: 10.1016/j.chembiol.2010.08.006
[3] PATRICK R SECOR. Phevalin (aureusimine B) production by Staphylococcus aureus biofilm and impacts on human keratinocyte gene expression.[J]. ACS Applied Bio Materials, 2012: e40973. DOI: 10.1371/journal.pone.0040973
[4] MORGAN A. WYATT. Staphylococcus aureus Nonribosomal Peptide Secondary Metabolites Regulate Virulence[J]. Science, 2010, 329 5989. DOI: 10.1126/science.1188888
3-(1-Methylethyl)-6-(phenylMethyl)-2(1H)-pyrazinone Preparation Products And Raw materials
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