Home>>(R)-3-Oxo-cyclopentaneacetic acid methyl ester

(R)-3-Oxo-cyclopentaneacetic acid methyl ester Sale

目录号 : GC46338

A neuropeptide with diverse biological activities

(R)-3-Oxo-cyclopentaneacetic acid methyl ester Chemical Structure

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50 mg
¥1,165.00
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产品描述

(R)-3-Oxo-cyclopentaneacetic acid methyl ester is a synthetic intermediate useful for pharmaceutical synthesis.

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Chemical Properties

Cas No. N/A SDF
Canonical SMILES O=C1C[C@H](CC(OC)=O)CC1
分子式 C8H12O3 分子量 156.2
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1 mM 6.402 mL 32.0102 mL 64.0205 mL
5 mM 1.2804 mL 6.402 mL 12.8041 mL
10 mM 0.6402 mL 3.201 mL 6.402 mL
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Research Update

Soil metagenome-derived 3-hydroxypalmitic acid methyl ester hydrolases suppress extracellular polysaccharide production in Ralstonia solanacearum

J Biotechnol 2018 Mar 20;270:30-38.PMID:29407418DOI:10.1016/j.jbiotec.2018.01.023.

Autoinducers are indispensable for bacterial cell-cell communication. However, due to the reliance on culture-based techniques, few autoinducer-hydrolyzing enzymes are known. In this study, we characterized soil metagenome-derived unique enzymes capable of hydrolyzing 3-hydroxypalmitic acid methyl ester (3-OH PAME), an autoinducer of the plant pathogenic bacterium Ralstonia solanacearum. Among 146 candidate lipolytic clones from a soil metagenome library, 4 unique enzymes capable of hydrolyzing the autoinducer 3-OH PAME, termed ELP86, ELP96, ELP104, and EstDL33, were selected and characterized. Phylogenetic analysis revealed that metagenomic enzymes were novel esterase/lipase candidates as they clustered as novel subfamilies of family I, V, X, and family XI. The purified enzymes displayed various levels of hydrolytic activities towards 3-OH PAME with optimum activity at 40-50 °C and pH 7-10. Interestingly, ELP104 also displayed N-(3-oxohexanoyl)-L-homoserine lactone hydrolysis activity. Heterologous expression of the gene encoding 3-OH PAME hydrolase in R. solanacearum significantly decreased exopolysaccharide production without affecting bacterial growth. mRNA transcription analysis revealed that genes regulated by quorum-sensing, such as phcA and xpsR, were significantly down-regulated in the stationary growth phase of R. solanacearum. Therefore, metagenomic enzymes are capable of quorum-quenching by hydrolyzing the autoinducer 3-OH PAME, which could be used as a biocontrol strategy against bacterial wilt.

Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake

Food Chem 2018 Nov 15;266:475-482.PMID:30381215DOI:10.1016/j.foodchem.2018.06.027.

Up to 35% of (R)-methyl 2-methylbutanoate (M2MB) was observed in a beverage fermented with shiitake. As M2MB naturally occurs typically in high excesses of the (S)-enantiomer, the origin of the (R)-ester was elucidated by stable isotope labeled precursor-feeding studies. (R)-2-Methylbutanoic acid was identified as the main precursor in the substrate wort. Trace amounts of (R)-M2MB were produced by transformation of unsaturated secondary metabolites (tiglic aldehyde and tiglic acid) derived from l-isoleucine. Surprisingly, shiitake esterified (R)-2-methylbutanoic acid faster to (R)-M2MB than the corresponding (S)-enantiomer. Concurrently, spontaneous non-enantioselective degradation of M2MB occurred in shiitake. This explains diverse enantiomeric ratios of M2MB and different enantiomeric ratios of 2-methylbutanoic acid and M2MB in the beverage. As the odor threshold values of (R)-and (S)-M2MB differ significantly, these findings are of high relevance for the overall flavor of the fermented beverage and elucidate the discrepancy of enantiomeric ratios of 2-alkyl-branched acids and esters reported in nature.

(R)-2-Benzyl-4-methyl-pentyl (R)-2-meth-oxy-2-(1-naphth-yl)propionate

Acta Crystallogr Sect E Struct Rep Online 2010 Jun 16;66(Pt 7):o1665.PMID:21587891DOI:10.1107/S160053681002101X.

The relative configuration of the alcohol component in the title ester, C(27)H(32)O(3), has been assigned as (R) from the known configuration of (R)-(-)-2-meth-oxy-2-(1-naphth-yl)propionic acid [(R)-MαNP acid]. In the crystal structure, the C atom of the methyl group of the MαNP acid lies in the extended plane of the naphthyl ring system [methyl C atom deviates from plane by 0.211 (2) Å; R.m.s. deviation of fitted atoms = 0.0187 Å] and a weak intra-molecular C-H⋯O hydrogen bond links the naphthyl ring system and the meth-oxy group. These structural properties are similar to those of most MαNP acid esters.

Enantioselective Resolution of (R, S)-2-Phenoxy-Propionic Acid Methyl Ester by Covalent Immobilized Lipase from Aspergillus oryzae

Appl Biochem Biotechnol 2020 Mar;190(3):1049-1059.PMID:31664700DOI:10.1007/s12010-019-03145-4.

(R)-2-Phenoxy-propionic acid methyl ester (PPAM) is an important chiral precursor of aryloxy phenoxy propionate herbicides. The covalent immobilization of lipase from Aspergillus oryzae WZ007 and the catalysis of enantioselective (R, S)-PPAM resolution by the immobilized A. oryzae lipase (AOL) were investigated in this study. The primary amino resin LX-1000HA was selected as the support for the covalent immobilization of AOL. The Km and Vmax of the immobilized lipase were 1.97 mM and 4.84 × 103 μmol/mg min, respectively. The key reaction parameters (pH, temperature, rotation speed, and substrate concentration) for the lipase-catalyzed resolution of (R, S)-PPAM were optimized. An e.e.s of 99.5% and conversion rate of 50.8% were achieved under the optimal conditions of pH 7.5, 30 °C, and substrate concentration 500 mM. The immobilized lipase retained 87.3% of its initial activity after 15 cycles of the repeated experiments. The results demonstrated that the covalent immobilized AOL has potential industrial applications.

Synthesis and Characterization of Novel Methyl (3)5-( N-Boc-piperidinyl)-1 H-pyrazole-4-carboxylates

Molecules 2021 Jun 22;26(13):3808.PMID:34206593DOI:10.3390/molecules26133808.

Series of methyl 3- and 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates were developed and regioselectively synthesized as novel heterocyclic amino acids in their N-Boc protected ester form for achiral and chiral building blocks. In the first stage of the synthesis, piperidine-4-carboxylic and (R)- and (S)-piperidine-3-carboxylic acids were converted to the corresponding β-keto esters, which were then treated with N,N-dimethylformamide dimethyl acetal. The subsequent reaction of β-enamine diketones with various N-mono-substituted hydrazines afforded the target 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates as major products, and tautomeric NH-pyrazoles prepared from hydrazine hydrate were further N-alkylated with alkyl halides to give 3-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates. The structures of the novel heterocyclic compounds were confirmed by 1H-, 13C-, and 15N-NMR spectroscopy and HRMS investigation.