Dissertation > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds

Plant cells enantioselective reduction of acenaphthene quinone

Author ZuoLianPeng
Tutor CuiJingNan
School Dalian University of Technology
Course Fine Chemicals
Keywords Biocatalysis Plant Cell Asymmetric reduction Acenaphthene quinone derivatives
CLC O621.2
Type Master's thesis
Year 2008
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Fused ring structure with a rigid chiral alcohols in pharmaceutical intermediates, transition metal ligands, analytical reagents, and the synthesis of functional materials has been widely applied. Stereoselective reduction of prochiral ketones preparation of chiral alcohols are the most important ways, but one rigid aromatic fused ring structure of a high steric hindrance tends to prevent the proximity chiral catalyst. So reducing polycyclic aromatic chemical methods to prepare the corresponding chiral ketone alcohol or a challenging task. In this paper, Acenaphthenequinone and substituted Acenaphthenequinone as substrate, using plant cells as biocatalysts, discover and implement the use of plant cell catalytic polycyclic aromatic ketones (Acenaphthenequinone with substituted Acenaphthenequinone) asymmetric reduction reaction to higher conversion rate and ee worth to the corresponding chiral alcohol compound. Catalytic substituted Acenaphthenequinone plant cells is carried out in a neutral aqueous solution, high-speed mechanical stirring conditions; reaction conversion rate and the ee value is determined using high performance liquid chromatography (HPLC) determination. Experimental results show that the plant cell catalytic reduction Acenaphthenequinone only get one hydroxy product, even if given enough time, there is no double-hydroxy-reduction product formation. Common in the selection of 15 plants, carrot (root) and peach (fruit) cells on substrates Acenaphthenequinone asymmetric reduction reaction is preferably catalytic effect (conversion rate: 96% ~ 98%, ee.: 75% ~ 81%). Surprising is that these two types of plant cells Acenaphthenequinone have opposite stereochemistry selectivity. Synthesis of substituted Acenaphthenequinone Acenaphthenequinone is a starting material, bromide, nitration, substituted, thermal decomposition and diazotization accomplished multi-step reaction. Carrot (root) and peach (fruit) cells catalytic reduction reaction of substituted Acenaphthenequinone also showed good regioselectivity, only to get a single hydroxy product. Moreover, these two types of plant cells to replace Acenaphthenequinone different catalytic reduction activity and stereoselectivity are very different (yield 0 ~ 52%, ee.: 48% ~ 81%). This is the first successful use of plant cells fused ring aromatic ketone compound catalyst (Acenaphthenequinone and substituted Acenaphthenequinone) reduction reaction of the plant cells expanded catalytic organic reactions range of substrates, the chiral alcohol condensed ring provides a compound new way. The fourth chapter of this thesis is based on the cobalt ion naphthalimide fluorescent probe (N1) Design and Synthesis of Research. Preliminary tests show, Co (Ⅱ) can cause fluorescence quenching fluorescence probe N1 and absorption spectra of redshift, ie N1 through dual-channel way to identify Co (Ⅱ). This part of the work is still not completed, further testing is still in progress.

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