Monoacetylphloroglucinol
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| Category | Others |
| Catalog number | BBF-03883 |
| CAS | 480-66-0 |
| Molecular Weight | 186.15 |
| Molecular Formula | C8H8O4 |
| Purity | >95% by HPLC |
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Description
Monoacetylphloroglucinol is a small molecular weight phenolic metabolite that belongs to the phloroglucinol (1,3,5-trihydroxybenzene) family produced by bacteria (including Pseudomonas strains). It exhibits a wide range of biological activities, although the potency is mostly low.
Specification
| Synonyms | 2,4,6-trihydroxyacetophemone |
| Storage | Store at -20°C |
| IUPAC Name | 1-(2,4,6-trihydroxyphenyl)ethanone |
| Canonical SMILES | CC(=O)C1=C(C=C(C=C1O)O)O |
| InChI | InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3 |
| InChI Key | XLEYFDVVXLMULC-UHFFFAOYSA-N |
| Source | Pseudomonas fluorescens |
Properties
| Appearance | White to Light Yellow Solid |
| Boiling Point | 333.2°C at 760 mmHg |
| Melting Point | 219-221°C(lit.) |
| Density | 1.446 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Water |
Reference Reading
1. Volatiles from the Mandibular Gland Reservoir Content of Colobopsis explodens Laciny and Zettel, 2018, Worker Ants (Hymenoptera: Formicidae)
Herbert Zettel, Rainer Schuhmacher, Alice Laciny, Michaela Hoenigsberger, Linda Bl Lim, Irina S Druzhinina, Alexey G Kopchinskiy, Kamariah A Salim, Christoph Bueschl, Alexandra Parich Molecules . 2019 Sep 24;24(19):3468. doi: 10.3390/molecules24193468.
Forty-five volatile organic compounds (VOCs) were identified or annotated in the mandibular gland reservoir content (MGRC) of the Southeast Asian antColobopsis explodensLaciny and Zettel, 2018 (Hymenoptera: Formicidae), using headspace solid-phase microextraction (HS-SPME) coupled to gas chromatography mass spectrometry (GC-MS) and liquid extraction combined with GC-MS. In extension of previous reports on VOCs ofC. explodens, members of different compound classes, such as alkanes, aliphatic and aromatic carboxylic acids, and phenolics, were detected. The ketone 2-heptanone and the biochemically related phenolics benzene-1,3,5-triol (phloroglucinol, PG), 1-(2,4,6-trihydroxyphenyl)ethanone (monoacetylphloroglucinol, MAPG), 5,7-dihydroxy-2-methylchromen-4-one (noreugenin), and 1-(3-Acetyl-2,4,6-trihydroxyphenyl)ethanone (2,4-diacetylphloroglucinol, DAPG) dominated the GC-MS chromatograms. The identities of the main phenolics MAPG and noreugenin were further verified by liquid chromatography-high resolution-tandem mass spectrometry (LC-HRMS/MS). A comparative study of MGRC samples originating from three distinct field expeditions revealed differences in the VOC profiles, but the presence and relative abundances of the dominating constituents were largely consistent in all samples. Our study considerably extends the knowledge about the number and type of VOCs occurring in the MGRC ofC. explodens. Based on the type of the detected compounds, we propose that the likely irritant and antibiotic phenolic constituents play a role in defense against arthropod opponents or in protection against microbial pathogens.
2. The putative compatible solute-binding protein ProX from Mycobacterium tuberculosis H37Rv: biochemical characterization and crystallographic data
Zhi Ping Wang, Yong Wang, Jiang Huai Chen, Jian Hong Zhao, Yong Xing He Acta Crystallogr F Struct Biol Commun . 2018 Apr 1;74(Pt 4):231-235. doi: 10.1107/S2053230X18003771.
In Mycobacterium tuberculosis, the proX gene encodes a putative compatible solute-binding protein (MtProX). However, it was found through sequence alignment that the MtProX protein has very different ligand-binding residues compared with other compatible solute-binding proteins, implying that MtProX may bind to ligands that are as yet uncharacterized. In this work, it was demonstrated that MtProX binds to polyphenols such as phloretin, monoacetylphloroglucinol and 2,4-dihydroxyacetophloroglucinol with dissociation constants between 20 and 70 µM. Crystals of MtProX were obtained using a precipitant consisting of 0.2 M NaCl, 0.1 M Tris pH 8.5, 25%(w/v) polyethylene glycol 3350. The crystals diffracted to 2.10 Å resolution and belonged to space group P43212, with unit-cell parameters a = b = 90.17, c = 161.92 Å, α = β = γ = 90.0°. Assuming the presence of two MtProX molecules in the asymmetric unit, the Matthews coefficient was calculated to be 2.74 Å3Da-1, which corresponds to a solvent content of 55%.
3. Mechanism of Biocatalytic Friedel-Crafts Acylation by Acyltransferase from Pseudomonas protegens
Masoud Kazemi, Anna Żądło-Dobrowolska, Xiang Sheng, Wolfgang Kroutil, Fahmi Himo ACS Catal . 2020 Jan 3;10(1):570-577. doi: 10.1021/acscatal.9b04208.
Acyltransferases isolated fromPseudomonas protegens(PpATase) andPseudomonas fluorescens(PfATase) have recently been reported to catalyze the Friedel-Crafts acylation, providing a biological version of this classical organic reaction. These enzymes catalyze the cofactor-independent acylation of monoacetylphloroglucinol (MAPG) to diacetylphloroglucinol (DAPG) and phloroglucinol (PG) and have been demonstrated to have a wide substrate scope, making them valuable for potential applications in biocatalysis. Herein, we present a detailed reaction mechanism ofPpATase on the basis of quantum chemical calculations, employing a large model of the active site. The proposed mechanism is consistent with available kinetics, mutagenesis, and structural data. The roles of various active site residues are analyzed. Very importantly, the Asp137 residue, located more than 10 Å from the substrate, is predicted to be the proton source for the protonation of the substrate in the rate-determining step. This key prediction is corroborated by site-directed mutagenesis experiments. Based on the current calculations, the regioselectivity ofPpATase and its specificity toward non-natural substrates can be rationalized.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
