- Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity
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Mincle, expressed in activated phagocytes, recognizes the lipid ligand to activate the innate immune system. We have synthesized glycerol derivatives possessing simple alkyl chains or aromatic rings and elucidated their structure-activity relationships us
- Matsumaru, Takanori,Ikeno, Risa,Shuchi, Yusuke,Iwamatsu, Toshiki,Tadokoro, Takashi,Yamasaki, Sho,Fujimoto, Yukari,Furukawa, Atsushi,Maenaka, Katsumi
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supporting information
p. 711 - 714
(2019/02/06)
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- Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes
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The enantioselective hydrolysis of different (RS)-1,2-O-isopropylidene glycerol esters has been achieved with whole cells of Bacillus coagulans NCIMB 9365 furnishing the (S)-alcohol as the major enantiomer. The reaction is catalysed by a thermostable cell-bound carboxylesterase and improvement of the enantioselectivity has been achieved by heat treatment of the whole cells, which causes the knock-outs a non-enantioselective competing enzyme. Thermally-treated cells hydrolysed (RS)-1,2-O-isopropylidene glycerol esters with high enantioselectivity, the highest enantiomeric ratio (80-100) being observed for the benzoate. The biocatalyst displayed good stability and could be re-used after filtration for 12 cycles before showing significant loss of activity; repeated biotransformation batches allowed the recovery of 9.55 g/L of enantiomerically pure (S)-isopropylideneglycerol benzoate starting from 24.0 g/L of the racemic mixture.
- Romano, Diego,Falcioni, Francesco,Mora, Diego,Molinari, Francesco,Buthe, Andreas,Ansorge-Schumacher, Marion
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p. 841 - 845
(2007/10/03)
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- Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
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Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied.
- Batovska, Daniela I.,Tsubota, Shuichirou,Kato, Yasuo,Asano, Yasuhisa,Ubukata, Makoto
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p. 3551 - 3559
(2007/10/03)
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- SUBSTRATE SPECIFICITY AND ENANTIOSELECTIVITY OF PENICILLINACYLASE CATALYZED HYDROLYSIS OF PHENACETYL ESTERS OF SYNTHETICALLY USEFUL CARBINOLS
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Penicillinacylase from E. coli, immobilized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23 deg C, of a set of O-phenylacetate esters of primary carbinols.The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework.Minor modifications of this basic structure are not altering the acceptability by the enzyme, but significantly decrease the enantioselectivity of the hydrolysis, as does the use of benzene as solvent and Sepharose-bound enzyme.
- Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Lazzarini, Ameriga,Casati, Paolo
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p. 2575 - 2582
(2007/10/02)
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