Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

被引：16

作者：

Borowiecki, Pawel ^{[1
]}

Bretner, Maria ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, PL-00664 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 15-16期

关键词：

CATALYZED KINETIC RESOLUTION; EFFICIENT ASYMMETRIC HYDROGENATION; FORMAL SYNTHESIS; ORGANIC-SOLVENTS; NOREPINEPHRINE TRANSPORTERS; SUBSTRATE-SPECIFICITY; PSEUDOMONAS-CEPACIA; MAJOR METABOLITE; BETA-KETOESTERS; ALDOL REACTION;

D O I：

10.1016/j.tetasy.2013.06.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：925 / 936

页数：12

共 103 条

[11]

Beck SG, 1997, J PHARMACOL EXP THER, V281, P115

[12] FLUOXETINE - A REVIEW OF ITS PHARMACODYNAMIC AND PHARMACOKINETIC PROPERTIES, AND THERAPEUTIC EFFICACY IN DEPRESSIVE-ILLNESS [J].

BENFIELD, P ;

HEEL, RC ;

LEWIS, SP .

DRUGS, 1986, 32 (06) :481-508

[13] ENZYMATIC-HYDROLYSIS OF ETHYL 3-HYDROXY-3-PHENYLPROPANOATE - OBSERVATIONS ON AN ENZYME ACTIVE-SITE MODEL [J].

BOAZ, NW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4289-4292

[14] Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin [J].

Bower, John F. ;

Riis-Johannessen, Thomas ;

Szeto, Peter ;

Whitehead, Andrew J. ;

Gallagher, Timothy .

CHEMICAL COMMUNICATIONS, 2007, (07) :728-730

[15] Lipase mediated sequential resolution of aromatic β-hydroxy esters using fatty acid derivatives [J].

Brem, Juergen ;

Naghi, Mara ;

Tosa, Monica-Ioana ;

Boros, Zoltan ;

Poppe, Laszlo ;

Irimie, Florin-Dan ;

Paizs, Csaba .

TETRAHEDRON-ASYMMETRY, 2011, 22 (16-17) :1672-1679

[16] Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: aspects on the preparation and enantiopreference [J].

Brem, Juergen ;

Liljeblad, Arto ;

Paizs, Csaba ;

Tosa, Monica Ioana ;

Irimie, Florin-Dan ;

Kanerva, Liisa T. .

TETRAHEDRON-ASYMMETRY, 2011, 22 (03) :315-322

[17] Enzyme-catalyzed synthesis of (R)- and (S)-3-hydroxy-3-(10-alkyl-10H-phenothiazin-3-yl)propanoic acids [J].

Brem, Juergen ;

Tosa, Monica Ioana ;

Paizs, Csaba ;

Vass, Elemer ;

Irimie, Florin Dan .

TETRAHEDRON-ASYMMETRY, 2010, 21 (03) :365-373

[18] Trends in the development of chiral drugs [J].

Caner, H ;

Groner, E ;

Levy, L ;

Agranat, I .

DRUG DISCOVERY TODAY, 2004, 9 (03) :105-110

[19] An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one [J].

Chaubey, Narendra R. ;

Ghosh, Sunil K. .

TETRAHEDRON-ASYMMETRY, 2012, 23 (15-16) :1206-1212

[20] [H-3]nisoxetine - A radioligand for noradrenaline reuptake sites: Correlation with inhibition of [H-3]noradrenaline uptake and effect of DSP-4 lesioning and antidepressant treatments [J].

Cheetham, SC ;

Viggers, JA ;

Butler, SA ;

Prow, MR ;

Heal, DJ .

NEUROPHARMACOLOGY, 1996, 35 (01) :63-70

← 1 2 3 4 5 6 7 8 9 10 →