SYNTHESIS OF CHIRAL BENZYL ALKYL SULFOXIDES BY CYCLOHEXANONE MONOOXYGENASE FROM ACINETOBACTER NCIB-9871

被引：26

作者：

PASTA, P

CARREA, G

HOLLAND, HL

DALLAVALLE, S

机构：

[1] BROCK UNIV,DEPT CHEM,ST CATHARINES,ON L2S 3A1,CANADA

[2] FAC FARM,IST CHIM ORGAN,MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 04期

关键词：

D O I：

10.1016/0957-4166(95)00102-U

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Benzyl alkyl sulfides with alkyl groups from methyl to hexyl, para-alkylbenzyl groups from methyl to butyl, 2-phenylethyl methyl sulfide and 3-phenylpropyl methyl sulfide have been oxidized by cyclohexanone monooxygenase from Acinetobacter NCIB 9871. Sulfoxides with enantiomeric excesses ranging from 80% for the (R)-configuration to 96% ee for the (S)-configuration were obtained.

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页码：933 / 936

页数：4

相关论文

共 10 条

[1] EFFECTS OF SUBSTRATE STRUCTURE ON THE ENANTIOSELECTIVITY AND STEREOCHEMICAL COURSE OF SULFOXIDATION CATALYZED BY CYCLOHEXANONE MONOOXYGENASE [J].

CARREA, G ;

REDIGOLO, B ;

RIVA, S ;

COLONNA, S ;

GAGGERO, N ;

BATTISTEL, E ;

BIANCHI, D .

TETRAHEDRON-ASYMMETRY, 1992, 3 (08) :1063-1068

[2]

DIFURIA F, 1984, SYNTHESIS-STUTTGART, P325

[3]

Holland H L, 1994, Bioorg Med Chem, V2, P647, DOI 10.1016/0968-0896(94)85013-5

[4] BIOTRANSFORMATION OF ORGANIC SULFIDES .5. FORMATION OF CHIRAL PARA-ALKYL BENZYL METHYL SULFOXIDES BY HELMINTHOSPORIUM SPECIES NRRL-4671 [J].

HOLLAND, HL ;

BROWN, FM ;

LARSEN, BG .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1241-1248

[5] CHIRAL SULFOXIDATION BY BIOTRANSFORMATION OF ORGANIC SULFIDES [J].

HOLLAND, HL .

CHEMICAL REVIEWS, 1988, 88 (03) :473-485

[6] MECHANISM-BASED INACTIVATION OF THE FLAVOENZYME CYCLOHEXANONE OXYGENASE DURING OXYGENATION OF CYCLIC THIOL ESTER SUBSTRATES [J].

LATHAM, JA ;

WALSH, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3421-3427

[7] THE ENANTIOSELECTIVE SYNTHESIS OF (-)-PHYSOSTIGMINE VIA CHIRAL SULFOXIDES [J].

MARINO, JP ;

BOGDAN, S ;

KIMURA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5566-5572

[8] A GENERAL-ROUTE TO ENANTIOMERICALLY PURE SULFOXIDES FROM A CHIRAL SULFITE [J].

REBIERE, F ;

SAMUEL, O ;

RICARD, L ;

KAGAN, HB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5991-5999

[9] ASYMMETRIC OXIDATION OF SULFIDES BY CYCLOHEXANONE MONOOXYGENASE [J].

SECUNDO, F ;

CARREA, G ;

DALLAVALLE, S ;

FRANZOSI, G .

TETRAHEDRON-ASYMMETRY, 1993, 4 (09) :1981-1982

[10]

SOLLADIE G, 1981, SYNTHESIS-STUTTGART, P185