Month: December 2022

Gordeev, Mikhail F. published the artcileNovel oxazolidinone-quinolone hybrid antimicrobials, Computed Properties of 924-99-2, the publication is Bioorganic & Medicinal Chemistry Letters (2003), 13(23), 4213-4216, database is CAplus and MEDLINE.

Antimicrobial compounds incorporating oxazolidinone and quinolone pharmacophore substructures have been synthesized and evaluated. Representative analogs I and II [racemic and 3-(S)-isomer] display an improved potency vs. linezolid against gram-pos. and fastidious gram-neg. pathogens. The compounds are also active against linezolid- and ciprofloxacin-resistant Staphylococcus aureus and Enterococcus faecium strains. The MOA for these new antimicrobials is consistent with a combination of protein synthesis and gyrase A/topoisomerase IV inhibition, with a structure-dependent degree of the contribution from each inhibitory mechanism.

Bioorganic & Medicinal Chemistry Letters published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C7H13NO2, Computed Properties of 924-99-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Tran, Van T. published the artcileActivation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalyzed β-X elimination, Recommanded Product: 3-Acetyldihydrofuran-2(3H)-one, the publication is Nature Chemistry (2018), 10(11), 1126-1133, database is CAplus and MEDLINE.

γ-Substituted N-(8-quinolinyl) alkanecarboxamides and cycloalkanecarboxamides such as I underwent regioselective substitution reactions with nucleophiles such as 1-methyl- and 1,2-dimethylindoles in the presence of Pd(OAc)₂ and 1-adamantanecarboxylic acid (1-AdCO₂H) to yield substitution products such as II (R = H, Me). The substitutions occurred using elimination reactions of the β-palladated carboxamides as a key step; a β-palladation product was isolated and its structure determined by X-ray crystallog. The substitution reactions occurred at alkyl C(sp³)-oxygen, nitrogen, carbon, fluorine and sulfur bonds with high regioselectivity. The method was used for substitution reactions of γ-substituted amino acids such as the 8-aminoquinolinyl amide of L-methionine and its sulfoxide to give functionalized amino acids in 60-98% ee. Unstrained 8-aminoquinolinyl heterocyclylalkanecarboxamides underwent regioselective γ-substitution reactions with ring opening if a heteroatom was in the γ-position; if the heteroatom was in an appropriate position, lactonization and lactamization reactions also occurred with loss of the aminoquinoline moieties.

Nature Chemistry published new progress about 517-23-7. 517-23-7 belongs to esters-buliding-blocks, auxiliary class Tetrahydrofuran,Ketone,Ester, name is 3-Acetyldihydrofuran-2(3H)-one, and the molecular formula is C18H28B2O4, Recommanded Product: 3-Acetyldihydrofuran-2(3H)-one.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Wu, Jian published the artcileImproving the Antigenicity of sTn Antigen by Modification of Its Sialic Acid Residue for Development of Glycoconjugate Cancer Vaccines, Application of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, the publication is Bioconjugate Chemistry (2006), 17(6), 1537-1544, database is CAplus and MEDLINE.

Sialyl Tn (sTn) antigen is a sialylated disaccharide abundantly expressed by many tumors. To search for effective cancer immunotherapies based on sTn antigen, the authors designed and synthesized a series of unnatural N-acyl derivatives of sTn and studied their immunol. properties. For this purpose, an efficient method was developed to synthesize the natural and unnatural forms of sTn antigen and their protein conjugates. The resultant glycoconjugates were used to immunize C57BL/6 mice, and the immune response was assessed by ELISA. Whereas the keyhole limpet hemocyanin (KLH) conjugate of sTn elicited low levels of IgM antibodies, the KLH conjugates of N-iso-butanoyl sTn and N-phenylacetyl sTn, especially the latter, induced high titers of antigen-specific IgG antibodies, showing a T-cell-dependent response that is critical for the antitumor activity. The results suggest that the modified forms of sTn, especially N-phenylacetyl sTn, have improved antigenicity and promising immunol. properties for use as cancer vaccines.

Bioconjugate Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C13H11NO, Application of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zhuang, Yuanhong published the artcilePreparation of functionalized pectin through acylation with alkyl gallates: Experiments coupled with density functional theory, COA of Formula: C10H12O5, the publication is International Journal of Biological Macromolecules (2022), 278-285, database is CAplus and MEDLINE.

The covalent grafting of alkyl gallates onto pectin using a lipase-catalyzed reaction in a tetrahydrofuran/aqueous medium process acylated pectin mols. with excellent antioxidant and antibacterial properties. The alkyl gallates including Me, Et, and Pr gallates were enzymically grafted onto pectin mol., in order to study the effect of alkyl gallates on the functional modification of pectin. The grafting mechanism was analyzed by UV-visible spectrum (UV-Vis), Fourier transform IR spectrum (FTIR), proton NMR (¹HNMR), and d. functional theory (DFT). Results suggested that lipase grafted 4-OH of alkyl gallate onto pectin by catalyzing esterification in organic/aqueous solution, and the grafting rate was affected by the length of alkyl chain of the gallates mol. In vitro experiments, the acylated pectins exhibited stronger antioxidant activity in the DPPH test and β-carotene bleaching test and were found to have obvious antimicrobial performance against Escherichia coli and Staphylococcus aureus.

International Journal of Biological Macromolecules published new progress about 121-79-9. 121-79-9 belongs to esters-buliding-blocks, auxiliary class Natural product, name is Propyl 3,4,5-trihydroxybenzoate, and the molecular formula is C6H10O7, COA of Formula: C10H12O5.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Xing, Minying published the artcileSynthesis of azobenzene functionalized dendritic block copolymer based on hyperbranched PDMAEMA and investigation of its drug release properties, COA of Formula: C23H28N2O4, the publication is Journal of Controlled Release (2011), 152(Suppl._1), e104-e105, database is CAplus and MEDLINE.

An azobenzene functionalized amphiphilic dendritic block copolymer based on hyperbranched poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA) was synthesized by the combination of AGET ATRP and self-condensing vinyl polymerization techniques. The degree of branching of hyperbranched PDMAEMA can be controlled by the initial molar ratio of inimer and monomer. The kinetic and chain extension investigation showed that the polymerization was living. Using chlorambucil as the model drug, the drug loaded block copolymer showed controlled chlorambucil release which was sensitive to both pH and light.

Journal of Controlled Release published new progress about 135529-02-1. 135529-02-1 belongs to esters-buliding-blocks, auxiliary class azo,Alkenyl,Benzene,Ester,Ether, name is 6-(4-((4-Methoxyphenyl)diazenyl)phenoxy)hexyl methacrylate, and the molecular formula is C11H15BF3N3O2, COA of Formula: C23H28N2O4.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Guo, Hao published the artcileContribution of odorant binding proteins to olfactory detection of (Z)-11-hexadecenal in Helicoverpa armigera, Name: (Z)-Dodec-9-en-1-yl acetate, the publication is Insect Biochemistry and Molecular Biology (2021), 103554, database is CAplus and MEDLINE.

Helicoverpa armigera utilizes (Z)-11-hexadecenal (Z11-16:Ald) as its major sex pheromone component. Three pheromone binding proteins (PBPs) and two general odorant binding proteins (GOBPs) are abundantly expressed in the male antennae of H. armigera. However, their precise roles in the olfactory detection of Z11-16:Ald remain enigmatic. To answer this question, we first synthesized the antibody against HarmOR13, an olfactory receptor (OR) primarily responding to Z11-16:Ald and mapped the local associations between PBPs/GOBPs and HarmOR13. Immunostaining showed that HarmPBPs and HarmGOBPs were localized in the supporting cells of trichoid sensilla and basiconic sensilla resp. In particular, HarmPBP1 and HarmPBP2 were colocalized in the cells surrounding the olfactory receptor neurons (ORNs) expressing HarmOR13. Next, using two noninterfering binary expression tools, we heterologously expressed HarmPBP1, HarmPBP2 and HarmOR13 in Drosophila T1 sensilla to validate the functional interplay between PBPs and HarmOR13. We found that the addition of HarmPBP1 or HarmPBP2, not HarmPBP3, significantly increased HarmOR13’s response to Z11-16:Ald. However, the presence of either HarmPBP1 or HarmPBP2 was ineffective to change the tuning breadth of HarmOR13 and modulate the response kinetics of this receptor. Taken together, this work demonstrates both HarmPBP1 and HarmPBP2 are involved in Z11-16:Ald detection. Our results support the idea that PBPs can contribute to the peripheral olfactory sensitivity but do little in modulating the selectivity and the response kinetics of corresponding ORs.

Insect Biochemistry and Molecular Biology published new progress about 16974-11-1. 16974-11-1 belongs to esters-buliding-blocks, auxiliary class Aliphatic Chain, name is (Z)-Dodec-9-en-1-yl acetate, and the molecular formula is C14H26O2, Name: (Z)-Dodec-9-en-1-yl acetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Qu, Lingzhi published the artcileCharacterization of the modification of Kelch-like ECH-associated protein 1 by different fumarates, Application of Dimethyl fumarate, the publication is Biochemical and Biophysical Research Communications (2022), 9-15, database is CAplus and MEDLINE.

Fumarates (fumaric acid esters), primarily di-Me fumarate (DMF) and monoethyl fumarate (MEF) and its salts, are orally administered systemic agents used for the treatment of psoriasis and multiple sclerosis. It is widely believed that the pharmaceutical activities of fumarates are exerted through the Keap1-Nrf2 pathway. Although it has been revealed that DMF and MEF differentially modify specific Keap1 cysteine residues and result in the differential activation of Nrf2, how the modification of DMF and MEF impacts the biochem. properties of Keap1 has not been well characterized. Here, we found that both DMF and MEF can only modify the BTB domain of Keap1 and that only C151 is accessible for covalent binding in vitro. Dynamic fluorescence scanning (DSF) assays showed that the modification of DMF to Keap1 BTB increased its thermal stability, while the modification of MEF dramatically decreased its thermal stability. Further crystal structures revealed no significant conformational variation between the DMF-modified and MEF-modified BTBs. Overall, our biochem. and structural study provides a better understanding of the covalent modification of fumarates to Keap1 and may suggest fundamentally different mechanisms adopted by fumarates in regulating the Keap1-Nrf2 pathway.

Biochemical and Biophysical Research Communications published new progress about 624-49-7. 624-49-7 belongs to esters-buliding-blocks, auxiliary class Inhibitor,Natural product, name is Dimethyl fumarate, and the molecular formula is C6H8O4, Application of Dimethyl fumarate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Feng, Liyan published the artcileVisible-Light-Induced Palladium-Catalyzed Intermolecular Narasaka-Heck Reaction at Room Temperature, Synthetic Route of 617-52-7, the publication is Organic Letters (2020), 22(10), 3964-3968, database is CAplus and MEDLINE.

A palladium-catalyzed Narasaka-Heck reaction by a domino cross-coupling reaction with aromatic alkenes under blue LED irradiation at room temperature was developed. The undesired β-hydride elimination of the hybrid alkyl palladium radical species was prohibited, enabling a broad range of oxime esters to undergo 5-exo cyclization and subsequent coupling with olefins. The practicality of the method was well illustrated by the construction of a nitrogen bridgehead tricycle as a core skeleton of alkaloids.

Organic Letters published new progress about 617-52-7. 617-52-7 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Aliphatic hydrocarbon chain,Ester, name is Dimethyl itaconate, and the molecular formula is C7H10O4, Synthetic Route of 617-52-7.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Huang, Shan-Shan published the artcileDimethyl itaconate alleviates the pyroptosis of macrophages through oxidative stress, Computed Properties of 617-52-7, the publication is BMC Immunology (2021), 22(1), 72, database is CAplus and MEDLINE.

Macrophages are involved in the pathophysiol. of many diseases as critical cells of the innate immune system. Pyroptosis is a form of macrophage death that induces cytokinesis of phagocytic substances in the macrophages, thereby defending against infection. Di-Me itaconate (DI) is an analog of itaconic acid with anti-inflammatory effects. However, the effect of di-Me itaconate on macrophage pyroptosis has not been elucidated clearly. Thus, the present study aimed to analyze the effect of DI treatment on a macrophage pyroptosis model (Lipopolysaccharide, LPS + ATP, ATP). The results showed that 0.25 mM DI ameliorated macrophage pyroptosis and downregulated interleukin (IL)-1β expression. Then, real-time quant. polymerase chain reaction (RT-qPCR) was used to confirm the result of RNA-sequencing of the upregulated oxidative stress-related genes (Gclc and Gss) and downregulated inflammation-related genes (IL-12β and IL-1β). In addition, Gene Ontol. (GO) enrichment anal. showed that differential genes were associated with transcript levels and DNA replication. Kyoto encyclopedia of genes and genomes (KEGG) enrichment showed that signaling pathways, such as tumor necrosis factor (TNF), Jak, Toll-like receptor and IL-17, were altered after DI treatment. N-acetyl-L-cysteine (NAC) reversed the DI effect on the LPS + ATP-induced macrophage pyroptosis and upregulated the IL-1β expression. Oxidative stress-related protein Nrf2 is involved in the DI regulation of macrophage pyroptosis. Taken together, these findings suggested that DI alleviates the pyroptosis of macrophages through oxidative stress.

BMC Immunology published new progress about 617-52-7. 617-52-7 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Aliphatic hydrocarbon chain,Ester, name is Dimethyl itaconate, and the molecular formula is C7H10O4, Computed Properties of 617-52-7.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Tao, Hui published the artcileMetabolic engineering of microbes for branched-chain biodiesel production with low-temperature property, Category: esters-buliding-blocks, the publication is Biotechnology for Biofuels (2015), 1-11, database is CAplus and MEDLINE.

Background: The steadily increasing demand for diesel fuels calls for renewable energy sources. This has attracted a growing amount of research to develop advanced, alternative biodiesel worldwide. Several major disadvantages of current biodiesels are the undesirable phys. properties such as high viscosity and poor low-temperature operability. Therefore, there is an urgent need to develop novel and advanced biodiesels. Results: Inspired by the proven capability of wax ester synthase/acyl-CoA, diacylglycerol acyltransferase (WS/DGAT) to generate fatty acid esters, de novo biosynthesis of fatty acid branched-chain esters (FABCEs) and branched fatty acid branched-chain esters (BFABCEs) was performed in engineered Escherichia coli through combination of the (branched) fatty acid biosynthetic pathway and the branched-chain amino acid biosynthetic pathway. Furthermore, by modifying the fatty acid pathway, we improved FABCE production to 273 mg/L and achieved a high proportion of FABCEs at 99.3 % of total fatty acid esters. In order to investigate the universality of this strategy, Pichia pastoris yeast was engineered and produced desirable levels of FABCEs for the first time with a good starting point of 169 mg/L. Conclusions: We propose new pathways of fatty acid ester biosynthesis and establish proof of concept through metabolic engineering of E. coli and P. pastoris yeast. We were able to produce advanced biodiesels with high proportions FABCEs and BFABCEs. Furthermore, this new strategy promises to achieve advanced biodiesels with beneficial low-temperature properties.

Biotechnology for Biofuels published new progress about 110-34-9. 110-34-9 belongs to esters-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Ester, name is Isobutyl palmitate, and the molecular formula is C13H18N2, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics