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Keywords = β-alkylation of secondary alcohols

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13 pages, 13478 KiB  
Article
Construction of a (NNN)Ru-Incorporated Porous Organic Polymer with High Catalytic Activity for β-Alkylation of Secondary Alcohols with Primary Alcohols
by Yao Cui, Jixian Wang, Lei Yu, Ying Xu, David J. Young, Haiyan Li and Hongxi Li
Polymers 2022, 14(2), 231; https://doi.org/10.3390/polym14020231 - 7 Jan 2022
Cited by 5 | Viewed by 2620
Abstract
Solid supports functionalized with molecular metal catalysts combine many of the advantages of heterogeneous and homogeneous catalysis. A (NNN)Ru-incorporated porous organic polymer (POP-bp/bbpRuCl3) exhibited high catalytic efficiency and broad functional group tolerance in the C–C cross-coupling of secondary and primary alcohols [...] Read more.
Solid supports functionalized with molecular metal catalysts combine many of the advantages of heterogeneous and homogeneous catalysis. A (NNN)Ru-incorporated porous organic polymer (POP-bp/bbpRuCl3) exhibited high catalytic efficiency and broad functional group tolerance in the C–C cross-coupling of secondary and primary alcohols to give β-alkylated secondary alcohols. This catalyst demonstrated excellent durability during successive recycling without leaching of Ru which is ascribed to the strong binding of the pincer ligands to the metal ions. Full article
(This article belongs to the Special Issue High Performance Porous Polymers)
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13 pages, 4503 KiB  
Article
Baeyer-Villiger-Including Domino Two-Step Oxidations of β-O-Substituted Primary Alcohols: Reflection of the Migratory Aptitudes of O-Substituted Alkyl Group in the Outcome of the Reaction
by Tom Targel and Moshe Portnoy
Catalysts 2020, 10(11), 1275; https://doi.org/10.3390/catal10111275 - 3 Nov 2020
Cited by 1 | Viewed by 3115
Abstract
Following the recent development of the one-pot two-step oxidation protocol for primary β-alkoxy alcohols, additional primary β-oxy alcohols were examined under similar conditions. The outcome of these reactions closely follows the migratory aptitudes of the related α-oxy-alkyls in Baeyer-Villiger oxidation vs. that of [...] Read more.
Following the recent development of the one-pot two-step oxidation protocol for primary β-alkoxy alcohols, additional primary β-oxy alcohols were examined under similar conditions. The outcome of these reactions closely follows the migratory aptitudes of the related α-oxy-alkyls in Baeyer-Villiger oxidation vs. that of hydrogen. Thus, these experiments helped to establish the correct order of these aptitudes for α-oxy-alkyls. Furthermore, in the case of primary β,β-dialkoxyalcohols, the formation of dialkoxymethyl formates by the domino oxidation reaction was followed by secondary reactions, forming a number of interesting products. Full article
(This article belongs to the Special Issue Organocatalysis: Advances, Opportunity, and Challenges)
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20 pages, 3764 KiB  
Article
A Novel Dimeric Exoglucanase (GH5_38): Biochemical and Structural Characterisation towards its Application in Alkyl Cellobioside Synthesis
by Mpho S. Mafa, Heinrich W. Dirr, Samkelo Malgas, Rui W. M. Krause, Konanani Rashamuse and Brett I. Pletschke
Molecules 2020, 25(3), 746; https://doi.org/10.3390/molecules25030746 - 9 Feb 2020
Cited by 6 | Viewed by 4224
Abstract
An exoglucanase (Exg-D) from the glycoside hydrolase family 5 subfamily 38 (GH5_38) was heterologously expressed and structurally and biochemically characterised at a molecular level for its application in alkyl glycoside synthesis. The purified Exg-D existed in both dimeric and monomeric forms in solution, [...] Read more.
An exoglucanase (Exg-D) from the glycoside hydrolase family 5 subfamily 38 (GH5_38) was heterologously expressed and structurally and biochemically characterised at a molecular level for its application in alkyl glycoside synthesis. The purified Exg-D existed in both dimeric and monomeric forms in solution, which showed highest activity on mixed-linked β-glucan (88.0 and 86.7 U/mg protein, respectively) and lichenin (24.5 and 23.7 U/mg protein, respectively). They displayed a broad optimum pH range from 5.5 to 7 and a temperature optimum from 40 to 60 °C. Kinetic studies demonstrated that Exg-D had a higher affinity towards β-glucan, with a Km of 7.9 mg/mL and a kcat of 117.2 s−1, compared to lichenin which had a Km of 21.5 mg/mL and a kcat of 70.0 s−1. The circular dichroism profile of Exg-D showed that its secondary structure consisted of 11% α-helices, 36% β-strands and 53% coils. Exg-D performed transglycosylation using p-nitrophenyl cellobioside as a glycosyl donor and several primary alcohols as acceptors to produce methyl-, ethyl- and propyl-cellobiosides. These products were identified and quantified via thin-layer chromatography (TLC) and liquid chromatography–mass spectrometry (LC-MS). We concluded that Exg-D is a novel and promising oligomeric glycoside hydrolase for the one-step synthesis of alkyl glycosides with more than one monosaccharide unit. Full article
(This article belongs to the Special Issue Green Compounds from Bio-Sources: Characterizations, Innovative Productions and Advanced Technological Applications)
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