53313-94-3Relevant academic research and scientific papers
Stabilization of Hydroxynitrile Lyases from Two Variants of Passion Fruit, Passiflora edulis Sims and Passiflora edulis Forma flavicarpa, by C-Terminal Truncation
Nuylert, Aem,Motojima, Fumihiro,Khanongnuch, Chartchai,Hongpattarakere, Tipparat,Asano, Yasuhisa
, p. 181 - 189 (2019/12/12)
Because the synthesis of chiral compounds generally requires a broad range of substrate specificity and stable enzymes, screening for better enzymes and/or improvement of enzyme properties through molecular approaches is necessary for sustainable industri
Highly chemoselective and efficient Strecker reaction of aldehydes with TMSCN catalyzed by MgI2 etherate under solvent-free conditions
He, Kailun,Liu, Huijun,Zhang, Xingxian,Zhou, Jing
supporting information, p. 933 - 936 (2019/03/08)
Strecker reaction of various substituted aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and α,β-unsaturated aldehydes with trimethylsilyl cyanide (TMSCN) was realized in the presence of 5 mol % of MgI2 etherate in a mild, efficient and highly chemoselective manner under solvent-free conditions.
Postfunctionalized Metalloligand-Based Catenated Coordination Polymers: Syntheses, Structures, and Effect of Labile Sites on Catalysis
Pandey, Saurabh,Kumar, Girijesh,Gupta, Rajeev
, p. 2723 - 2735 (2019/05/01)
In this work, pyridyl-appended Co3+ complexes (1 and 2) have been postfunctionalized by using 4-(bromomethyl)benzoic acid, thus changing the functionalities from pyridyl-N donors to carboxylate-O donors. Using two such postfunctionalized metalloligands (3 and 4), several homo and heterometallic coordination polymers (HCPs) have been synthesized. Single crystal structural analyses revealed that all HCPs presented intriguing one-dimensional catenated architectures. Postsynthetic modification induced flexibility was found to be responsible for the nearly identical architectures for two sets of HCPs starting from two different postfunctionalized metalloligands, 3 and 4. Two sets of HCPs differed by the presence (3a-3d) or absence (4a-4b) of labile coordinated water molecules that demonstrated a profound effect on the heterogeneous catalysis of Knoevenagel condensation reactions and cyanation reactions.
Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications
Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei
, p. 1185 - 1193 (2017/04/13)
Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).
Multivariate Metal-Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions
Xia, Qingchun,Li, Zijian,Tan, Chunxia,Liu, Yan,Gong, Wei,Cui, Yong
supporting information, p. 8259 - 8266 (2017/06/28)
The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural series of 2-fold interpenetrated MTV-MOFs that contain up to three different chiral metallosalen catalysts was constructed and used as efficient and recyclable heterogeneous catalysts for a variety of asymmetric sequential alkene epoxidation/epoxide ring-opening reactions. Interpenetration of the frameworks brings metallosalen units adjacent to each other, allowing cooperative activation, which results in improved efficiency and enantioselectivity over the sum of the individual parts. The fact that manipulation of molecular catalysts in MTV-MOFs can control the activities and selectivities would facilitate the design of novel multifunctional materials for enantioselective processes.
A magnetic nanoparticle catalyzed eco-friendly synthesis of cyanohydrins in a deep eutectic solvent
Azizi, Najmedin,Rahimi, Zahra,Alipour, Masoumeh
, p. 61191 - 61198 (2015/07/28)
Magnetic Fe3O4 nanoparticles in deep eutectic solvents (DESs) have been regard as excellent catalysts for highly efficient cyanosilylation of various aldehydes and epoxides using trimethylsilyl cyanide TMSCN in high yields with excellent selectivity. Fe3O4 nanoparticles were synthesized and applied as a catalyst for the preparation of a wide variety of cyanohydrins (α-hydroxy nitriles and β-hydroxy nitriles) in readily available urea-choline chloride deep eutectic solvent DES as the most promising environmentally benign and cost-effective green solvent. Magnetic DES operates at very mild reaction conditions and can be easily recycled without significant loss of its catalytic activity.
A metalloligand appended with thiazole rings: Heterometallic {Co3+-Zn2+} and {Co3+-Cd2+} complexes and their heterogeneous catalytic applications
Bansal, Deepak,Hundal, Geeta,Gupta, Rajeev
, p. 1022 - 1032 (2015/06/24)
This work describes a Co3+-based metalloligand containing appended thiazole rings and its reactions with secondary metal ions to produce heterometallic {Co3+-Zn2+} and {Co3+-Cd2+} complexes. Structural studies show that some of the appended thiazole rings from the metalloligand coordinate to secondary metal ions, whereas the remaining ones act as hydrogen-bond acceptors to metal-bound CH3OH or H2O molecules. These heterometallic complexes function as reusable heterogeneous catalysts for the ring-opening reactions of epoxides as well as cyanation and Knoevenagel condensation reactions of aldehydes. The catalytic results illustrate that the microenvironment remains intact during the catalysis and potentially enhances the substrate interaction with the Lewis acidic secondary metal ions.
Three-Dimensional Heterometallic Coordination Networks: Syntheses, Crystal Structures, Topologies, and Heterogeneous Catalysis
Srivastava, Sumit,Aggarwal, Himanshu,Gupta, Rajeev
, p. 4110 - 4122 (2015/08/18)
This work presents the synthesis of {Co3+-Zn2+} and {Co3+-Cd2+} heterometallic coordination networks. These networks are originated from two unique Co3+-based metalloligands containing appended arylcarboxylic acid groups at the strategically placed positions. Such appended arylcarboxylate groups coordinate the secondary metal ions, Zn2+ and Cd2+, to afford distinct three-dimensional networks. All four networks display orderly arrangement of secondary metal ions and unique network topologies including an unprecedented one. These networks have been shown to act as the heterogeneous and reusable catalysts for the Knoevenagel condensation reactions and cyanation reactions of assorted aldehydes. Cyanation reactions nicely demonstrate the substrate size-exclusion catalysis.
Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes
B?ocka, Ewelina,Bosiak, Mariusz J.,We?niak, Miros?aw,Ludwiczak, Agnieszka,Wojtczak, Andrzej
, p. 554 - 562 (2014/05/06)
Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino- 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes
Relationships between the racemic structures of substituted mandelic acids containing 8- and 10-membered hydrogen bonded dimer rings
Coles,Ellis,Leung,Sarson,Threlfall,Tizzard
, p. 10816 - 10823 (2015/02/19)
The structures of 27 monosubstituted mandelic acids, including several of their polymorphs, plus unsubstituted mandelic acid itself (two polymorphs) are investigated for structural similarity. The results, presented pictorially as a structural relationship plot, show that rather more structures are built up from the carboxyl-chain hydroxyl hydrogen bonded dimer than from the conventional carboxylic acid dimer. The results show how all the structures are related and, based on the two types of dimer, the degree of similarity that they possess. Some structures with Z′ > 1 contain both sorts of dimers and there are many examples of isostructural sets within the structures so far determined. We also present an example where analysing similarity in related families of structures highlights a structure that should be present and which has indeed then proceeded to be synthesised and determined.
