530-59-6Relevant articles and documents
Activities of Arabidopsis sinapoylglucose:malate sinapoyltransferase shed light on functional diversification of serine carboxypeptidase-like acyltransferases
Stehle, Felix,Brandt, Wolfgang,Schmidt, Juergen,Milkowski, Carsten,Strack, Dieter
, p. 1826 - 1831 (2008)
Analysis of the catalytic properties of the serine carboxypeptidase-like (SCPL) 1-O-sinapoyl-β-glucose:l-malate sinapoyltransferase (SMT) from Arabidopsis showed that the enzyme exhibits besides its primary sinapoylation of l-malate, minor hydrolytic and disproportionation activities, producing free sinapic acid and 1,2-di-O-sinapoyl-β-glucose, respectively. The ability of the enzyme to liberate sinapic acid from the donor molecule 1-O-sinapoyl-β-glucose indicates the existence of a short-lived acylenzyme intermediate in the proposed random sequential bi-bi mechanism of catalysis. SMT-catalyzed formation of disinapoylglucose has been corroborated by docking studies with an established homology structure model that illustrates the possible binding of two 1-O-sinapoyl-β-glucose molecules in the active site and the intermolecular reaction of the two glucose esters. The SMT gene is embedded in a tandem cluster of five SCPL sinapoyltransferase genes, which encode enzymes with high amino acid sequence identities and partially overlapping substrate specificities. We assume that in recent duplications of genes encoding SCPL proteins, neofunctionalization of the duplicates to accept 1-O-sinapoyl-β-glucose as acyl donor was gained first, followed by subfunctionalization leading to different acyl acceptor specificities.
Noda,Matsumoto
, p. 131 (1971)
Dependency of the hydrogen bonding capacity of the solvent anion on the thermal stability of feruloyl esterases in ionic liquid systems
Zeuner, Birgitte,Stahlberg, Tim,Van Buu, Olivier Nguyen,Kunov-Kruse, Andreas Jonas,Riisager, Anders,Meyer, Anne S.
, p. 1550 - 1557 (2011)
Three feruloyl esterases, EC 3.1.1.73, (FAEs), namely FAE A from Aspergillus niger (AnFaeA), FAE C from Aspergillus nidulans (AndFaeC), and the FAE activity in a commercial β-glucanase mixture from Humicola insolens (Ultraflo L) were tested for their ability to catalyse esterification of sinapic acid with glycerol in four ionic liquid (IL) systems. The IL systems were systematically composed of two selected pairs of cations and anions, respectively: [BMIm][PF6], [C2OHMIm][PF6], [BMIm][BF4], and [C2OHMIm][BF4]. AnFaeA had activity in [PF6]--based ILs, whereas the AndFaeC and the FAE in Ultraflo L had no appreciable activities and were generally unstable in the IL systems. FAE stability in the IL systems was apparently highly dependent on enzyme structure, and notably AnFaeA's similarity to IL-compatible lipases may explain its stability. The thermal stability of AnFaeA was higher in buffer than in the IL systems, but at 40 °C and below there was no significant difference in AnFaeA stability between the buffer and the [PF6] --based systems: AnFaeA was stable in the [BMIm][PF6] and [C2OHMIm][PF6] systems for 2 h at 40 °C. However, the IL anion had a major effect on stability: [BF4]- caused rapid inactivation of AnFaeA, while [PF6]- did not. The cation did not have a similar effect. These observations could be explained in terms of the hydrogen bonding capacity of IL cations and anions via COSMO-RS simulations.
Amino Group Functionalized Hf-Based Metal-Organic Framework for Knoevenagel-Doebner Condensation
Das, Aniruddha,Anbu, Nagaraj,Gogoi, Chiranjib,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
, p. 3396 - 3403 (2021/08/20)
A Hf(IV) metal-organic framework (MOF) with di-amino functionalized linker was obtained as a crystalline solid with UiO-67 topology under solvothermal reaction conditions. The guest free form of Hf(IV) MOF (1′) was efficiently employed as a heterogeneous catalyst to synthesize cinnamic acid derivatives via Knoevenagel-Doebner reaction for the first time. The catalyst (1′) was efficiently active to directly achieve cinnamic acid from benzaldehyde and malonic acid. The solid retained its activity up to 6th cycle with no decay in its activity. The noticeable advantages of the catalyst are its milder reaction conditions, high yield, high stability, recyclable nature towards catalysis and wide substrate scope as well as shape-selective behaviour. The possible mechanism of the reaction was also studied thoroughly with suitable control experiments.
Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min
supporting information, p. 2866 - 2874 (2021/11/12)
Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.
Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
supporting information, p. 8829 - 8842 (2021/06/30)
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.