Asymmetric synthesis of arylselenoalcohols by means of the reduction of organoseleno acetophenones by whole fungal cells

被引：25

作者：

Andrade, LH ^{[1
]}

Omori, AT ^{[1
]}

Porto, ALM ^{[1
]}

Comasseto, JV ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, Lab Quim Fina & Biocatalise, BR-05508900 Sao Paulo, Brazil

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2004年 / 29卷 / 1-6期

关键词：

microbial reduction; whole fungal cells; ketones; selenium; alcohols;

D O I：

10.1016/j.molcatb.2004.01.014

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of novel organoseleno acetophenones (3a-f) have been synthesized. The microbial reduction of the seleno ketones (3) has been evaluated using whole cells of Rhizopus oryzae CCT 4964, Aspergillus terreus CCT 3320, A. terreus CCT 4083 and Emericella nidulans CCT 3119. These microorganisms showed Prelog and anti-Prelog stereoselectivity, leading to the arylselenoalcohols in moderate to high enantiomeric excesses. The organoselenium compounds were compatible with the biocatalytic conditions employed. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：47 / 54

页数：8

共 38 条

[1]

ANDRADE LH, 2000, TETRAHEDRON LETT, V41, P161

[2]

ANDRADE LH, 2000, SYNTHETIC COMMUN, V30, P407

[3]

ANDRADE LH, 1997, SYNLETT, V5, P595

[4]

ANDRADE LH, 1998, SYNTHESIS-STUTTGART, V1, P39

[5]

[Anonymous], BIOCATALYSTS FINE CH

[6]

Back T. G., 1999, ORGANOSELENIUM CHEM

[7] FUNCTIONAL-GROUP DIVERSITY IN ENZYMATIC OXYGENATION REACTIONS CATALYZED BY BACTERIAL FLAVIN-CONTAINING CYCLOHEXANONE OXYGENASE [J].

BRANCHAUD, BP ;

WALSH, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2153-2161

[8] PREPARATION AND DIELS-ALDER REACTIVITY OF SEVERAL NEW CHALCOGEN-HALOGEN SUBSTITUTED BUTADIENES [J].

BRIDGES, AJ ;

FISCHER, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) :2954-2961

[9] First evaluation of the Brazilian microorganisms biocatalytic potential [J].

Cagnon, JR ;

Porto, ALM ;

Marsaioli, AJ ;

Manfio, GP ;

Eguchi, SY .

CHEMOSPHERE, 1999, 38 (10) :2237-2242

[10] Bioreduction of fluoroacetophenones by the fungi Aspergillus terreus and Rhizopus oryzae [J].

Comasseto, JV ;

Omori, AT ;

Andrade, LH ;

Porto, ALM .

TETRAHEDRON-ASYMMETRY, 2003, 14 (06) :711-715

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