Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases

被引：12

作者：

Bonomi, Paolo ^{[1
,2
]}

Cairoli, Paola ^{[1
,2
]}

Ubiali, Daniela ^{[3
,4
]}

Morelli, Carlo F. ^{[1
,2
]}

Filice, Marco ^{[3
,4
]}

Nieto, Ines ^{[3
,4
,5
,6
]}

Pregnolato, Massimo ^{[3
,4
]}

Manitto, Paolo ^{[1
,2
]}

Terreni, Marco ^{[3
,4
]}

Speranza, Giovanna ^{[1
,2
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] Italian Biocatalysis Ctr, I-20133 Milan, Italy

[3] Univ Pavia, Pharmaceut Biocatalysis Labs, Dipartimento Chim Farmaceut, I-27100 Pavia, Italy

[4] Italian Biocatalysis Ctr, I-27100 Pavia, Italy

[5] Innovate Biotechnol Srl, I-15050 Rivalta Scrivia, AL, Italy

[6] Italian Biocatalysis Ctr, I-15050 Rivalta Scrivia, AL, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 04期

关键词：

MICROBIAL REDUCTION; DOPAMINE-D-2; BIOREDUCTION; BINDING; KETONES; D-3;

D O I：

10.1016/j.tetasy.2009.02.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(R)-2-Tetralol (R)-2a, (R)-5-hydroxy-2-tetralol (R)-2b and (R)-8-hydroxy-2-tetralol (R)-2c, which are key intermediates in the synthesis of pharmacologically active 2-aminotetralins 3, were prepared in moderate to very high enantiomeric excess (up to 99% ee) by enzymatic resolution of the corresponding racemic butyrates rac-1a, rac-1b and rac-1c, respectively, using lipases immobilized on octyl agarose. This methodology is an alternative to the microbial reduction of 2-tetralones. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：467 / 472

页数：6

共 27 条

[1] Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones [J].

Abalain, C ;

Buisson, D ;

Azerad, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2983-2996

[2] Asymmetric bioreduction of racemic 5,4,7,8-tetrahydro-8-methyl-1,3-dimethoxynaphthalen-6-one to the corresponding chiral β-tetralols [J].

Aina, G ;

Nasini, G ;

de Pava, OV .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) :367-371

[3] 8-HYDROXY-2-(ALKYLAMINO)TETRALINS AND RELATED-COMPOUNDS AS CENTRAL 5-HYDROXYTRYPTAMINE RECEPTOR AGONISTS [J].

ARVIDSSON, LE ;

HACKSELL, U ;

JOHANSSON, AM ;

NILSSON, JLG ;

LINDBERG, P ;

SANCHEZ, D ;

WIKSTROM, H ;

SVENSSON, K ;

HJORTH, S ;

CARLSSON, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (01) :45-51

[4] ASYMMETRIC MICROBIAL REDUCTION OF TETRALONES [J].

BEGUE, JP ;

CERCEAU, C ;

DOGBEAVOU, A ;

MATHE, L ;

SICSIC, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (22) :3141-3144

[5]

Beyreuther B., 2007, PCT Int. Appl., Patent No. [WO 2007147556 A1 20071227, 2007147556]

[6]

BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3

[7] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[8] 2-AMIDO-8-METHOXYTETRALINS - A SERIES OF NONINDOLIC MELATONIN-LIKE AGENTS [J].

COPINGA, S ;

TEPPER, PG ;

GROL, CJ ;

HORN, AS ;

DUBOCOVICH, ML .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2891-2898

[9] A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments:: Binding activity at D2 and D3 receptors [J].

Dutta, AK ;

Fei, XS ;

Reith, MEA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (04) :619-622

[10] 2-aminotetralin-derived substituted benzamides with mixed dopamine D2, D3, and serotonin 5-HT1A receptor binding properties:: A novel class of potential atypical antipsychotic agents [J].

Homan, EJ ;

Copinga, S ;

Elfström, L ;

van der Veen, T ;

Hallema, JP ;

Mohell, N ;

Unelius, L ;

Johansson, R ;

Wikström, HV ;

Grol, CJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (11) :2111-2126

← 1 2 3 →