208988-63-0Relevant academic research and scientific papers
Fluorescent and Biocompatible Ruthenium-Coordinated Oligo(p-phenylenevinylene) Nanocatalysts for Transfer Hydrogenation in the Mitochondria of Living Cells
Chen, Yanyan,Dai, Nan,Liu, Libing,Lv, Fengting,Qi, Ruilian,Wang, Shu,Zhao, Hao
, (2020)
It is challenging to design metal catalysts for in situ transformation of endogenous biomolecules with good performance inside living cells. Herein, we report a multifunctional metal catalyst, ruthenium-coordinated oligo(p-phenylenevinylene) (OPV-Ru), for intracellular catalysis of transfer hydrogenation of nicotinamide adenine dinucleotide (NAD+) to its reduced format (NADH). Owing to its amphiphilic characteristic, OPV-Ru possesses good self-assembly capability in water to form nanoparticles through hydrophobic interaction and π–π stacking, and numerous positive charges on the surface of nanoparticles displayed a strong electrostatic interaction with negatively charged substrate molecules, creating a local microenvironment for enhancing the catalysis efficiency in comparison to dispersed catalytic center molecule (TOF value was enhanced by about 15 fold). OPV-Ru could selectively accumulate in the mitochondria of living cells. Benefiting from its inherent fluorescence, the dynamic distribution in cells and uptake behavior of OPV-Ru could be visualized under fluorescence microscopy. This work represents the first demonstration of a multifunctional organometallic complex catalyzing natural hydrogenation transformation in specific subcellular compartments of living cells with excellent performance, fluorescent imaging ability, specific mitochondria targeting and good chemoselectivity with high catalysis efficiency.
O-bicyclic amine compounds as well as preparation method and chiral products thereof
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Paragraph 0150; 0210, (2017/11/04)
The invention relates to the field of asymmetric synthesis methods, and discloses a preparation method of o-bicyclic amine compounds. The method comprises the step of enabling a compound having a structure as shown in a formula (1) and hydrogen to be subjected to an addition reaction in presence of a chiral catalyst, wherein the chiral catalyst is a complex having a structure as shown in a formula (2). The invention also provides chiral products of the o-bicyclic amine compounds prepared by the method, and the o-bicyclic amine compounds. After the method is adopted, the selective hydrogenation reduction of the compound having the structure as shown in the formula (1) is realized by using the hydrogen, so that octahydrogenated products, i.e., the o-bicyclic amine compounds shown in a formula (4) are produced with low cost. The formula (1), the formula (2) and the formula (4) are described in the description.
SELECTIVE TRANSFER HYDROGENATION OF CITRAL OR ETHYL CITRAL
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Page/Page column 18, (2015/02/02)
The present invention relates to a selective transfer hydrogenation of citral to geraniol/nerol and ethyl citral to ethyl geraniol/ethyl nerol.
SELECTIVE TRANSFER HYDROGENATION OF RETINAL
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Page/Page column 18, (2015/02/02)
The present invention relates to a selective transfer hydrogenation of retinal to retinol.
SELECTIVE TRANSFER HYDROGENATION OF CITRAL OR ETHYL CITRAL
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Page/Page column 18, (2015/02/02)
The present invention relates to a selective transfer hydrogenation of citral to geraniol/nerol and ethyl citral to ethyl geraniol/ethyl nerol.
Improved catalytic activity of ruthenium-arene complexes in the reduction of NAD+
Soldevila-Barreda, Joan J.,Bruijnincx, Pieter C. A.,Habtemariam, Abraha,Clarkson, Guy J.,Deeth, Robert J.,Sadler, Peter J.
, p. 5958 - 5967 (2012/11/07)
A series of neutral RuII half-sandwich complexes of the type [(η6-arene)Ru(N,N′)Cl] where the arene is para-cymene (p-cym), hexamethylbenzene (hmb), biphenyl (bip), or benzene (bn) and N,N′ is N-(2-aminoethyl)-4-(trifluoromethyl)benzenesulfonamide (TfEn), N-(2-aminoethyl)-4-toluenesulfonamide (TsEn), or N-(2-aminoethyl) methylenesulfonamide (MsEn) were synthesized and characterized. X-ray crystal structures of [(p-cym)Ru(MsEn)Cl] (1), [(hmb)Ru(TsEn)Cl] (5), [(hmb)Ru(TfEn)Cl] (6), [(bip)Ru(MsEn)Cl] (7), and [(bip)Ru(TsEn)Cl] (8) have been determined. The complexes can regioselectively catalyze the transfer hydrogenation of NAD + to give 1,4-NADH in the presence of formate. The turnover frequencies (TOF) when the arene is varied decrease in the order bn > bip > p-cym > hmb for complexes with the same N,N′ chelating ligand. The TOF decreased with variation in the N,N′ chelating ligand in the order TfEn > TsEn > MsEn for a given arene. [(bn)Ru(TfEn)Cl] (12) was the most active, with a TOF of 10.4 h-1. The effects of NAD+ and formate concentration on the reaction rates were determined for [(p-cym)Ru(TsEn)Cl] (2). Isotope studies implicated the formation of [(arene)Ru(N,N′)(H)] as the rate-limiting step. The coordination of formate and subsequent CO2 elimination to generate the hydride were modeled computationally by density functional theory (DFT). CO2 elimination occurs via a two-step process with the coordinated formate first twisting to present its hydrogen toward the metal center. The computed barriers for CO2 release for arene = benzene follow the order MsEn > TsEn > TfEn, and for the MsEn system the barrier followed bn A study of pH dependence of the reaction in D2O gave the optimum pH* as 7.2 with a TOF of 1.58 h-1 for 2. The series of compounds reported here show an improvement in the catalytic activity by an order of magnitude compared to the ethylenediamine analogues.
