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JOURNAL OF CATALYSIS · 2017 · IF 6.844

Oxidative C(OH)C bond cleavage of secondary alcohols to acids over a copper catalyst with molecular oxygen as the oxidant

Min Wang,Jianmin Lu,Lihua Li,Hongji Li,Huifang Liu,Feng Wang

Selective oxidative cleavage of C C bond is pivotal for producing functionalized molecules, useful for organic synthesis and biomass utilization. We herein report the oxidative C(OH) C bond cleavage of secondary alcohols to acids over a copper/1, 10-phenanthroline complex with molecular oxygen as the oxidant. A wide range of secondary alcohols are converted into acids with up to 98% yields. More interestingly, it is effective for breaking up lignin model systems into acids, which is rarely achieved in previous studies. Density functional theory (DFT) calculations indicate a copper-oxo-bridged oxygen dimer is the active species for the C H bond cleavage which is the rate-determining step for C C bond.

研究领域: 有机化学 · 催化化学

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PROCESS BIOCHEMISTRY · 2024 · IF 3.7

Enhanced catalytic efficiency for chiral alcohol pharmaceutical intermediate production using polyacrylic acid (PAA)-based nano-bienzyme conjugates at the organic-buffer biphasic interface

Pengpeng Cheng,Zhenyu He,Bo Liu,Jinmei Wang,Chuyue Zhang,Lan Tang,Lihua Du,Yuan Lu,Zhimin Ou

Nano-bienzyme conjugates (nano-BECs) for catalysing one-pot reactions can simplify the reaction process and improve the efficiency of biocatalytic reactions. In this work glucose dehydrogenase (GDH) and Candida parapsilosis secondary alcohol dehydrogenase (CpSADH) were immobilised with polyacrylic acid (PAA) to form two types of PAA-based nano-BECs (2-S, 2-P), which achieved in situ regeneration of NADH for the production of chiral alcohols in oil-water biphasic systems, such as the key chiral pharmaceutical intermediate of ( S )-1-(3-trifluoromethylphenyl)ethanol (( S )-TMPE). At a substrate concentration of 100 mM 3-trifluoromethylacetophenone (TMAP), the conversion catalyzed by nano BEC was 98.2 % in dipentyl phthalate-phosphate buffer biphasic system. In contrast, the conversion was only 39.5 % and 38.9 % in the PB buffer and 8.4 % and 7.7 % in dipentyl phthalate system. The experiments on kinetic constants demonstrated that the catalytic efficiencies (K cat /K m ) of nano-BECs (2-S, 2-P) were enhanced by 6.7-fold and 7-fold, respectively, compared to free CpSADH. Additionally, nano-BECs showed stronger coenzyme regeneration ability. Under optimal reaction conditions, nano-BECs achieved 96.2 % conversion of TMAP to ( S )-TMPE in an organic-buffer system with e.e. > 99.6 % at 300 mM substrate concentration. This research expands the potential applications of polymers and proteins, and offers valuable insights into the synergistic effects of PAA on bienzyme catalytic systems in biocatalysis.

CAS / MDL: 25952-53-8 9003-01-4

研究领域: 生物催化 · 药物化学 · 材料科学 · 酶学

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Oxidative C(OH)C bond cleavage of secondary alcohols to acids over a copper catalyst with molecular oxygen as the oxidant

Enhanced catalytic efficiency for chiral alcohol pharmaceutical intermediate production using polyacrylic acid (PAA)-based nano-bienzyme conjugates at the organic-buffer biphasic interface