Enantioselective oxidation of sulfides to sulfoxides catalysed by bacterial cyclohexanone monooxygenases

被引：88

作者：

Colonna, S ^{[1
]}

Gaggero, N ^{[1
]}

Pasta, P ^{[1
]}

Ottolina, G ^{[1
]}

机构：

[1] CNR,IST CHIM ORMONI,I-20131 MILAN,ITALY

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 20期

关键词：

D O I：

10.1039/cc9960002303

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This review article briefly introduces the applications of bacterial cyclohexanone monooxygenases to the enantioselective oxidations of organic sulfur compounds to sulfoxides, High enantioselectivities are observed in the sulfoxidation of alkyl aryl sulfides, disulfides, dialkyl sulfides, cyclic and acyclic 1,3-dithioacetals, The oxidation of ail;yl aryl sulfides with flavin dependent microorganisms extends the synthetic interest of this class of enzymes.

引用

页码：2303 / 2307

页数：5

共 33 条

[1] ABUSHANAB E, 1978, TETRAHEDRON LETT, V37, P3415
[2] TRANS-1,3-DITHIANE-1,3-DIOXIDE, A NEW CHIRAL ACYL ANION EQUIVALENT FOR THE PREPARATION OF MASKED ACTIVATED ACIDS - APPLICATION TO THE SYNTHESIS OF ALPHA-HYDROXY ACID-DERIVATIVES
AGGARWAL, VK
THOMAS, A
FRANKLIN, RJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (14) : 1653 - 1654
[3] CHIRAL, BISFUNCTIONALIZATION OF SUBSTRATES - A POWERFUL STRATEGY FOR THE ASYMMETRIC-SYNTHESIS OF C2 SYMMETRIAL COMPOUNDS AND ITS APPLICATION TO THE SYNTHESIS OF ENANTIOMERICALLY PURE TRANS-1,3-DITHIANE 1,3-DIOXIDE
AGGARWAL, VK
EVANS, G
MOYA, E
DOWDEN, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6390 - 6391
[4] ALLEN CCR, 1995, J CHEM SOC CHEM COMM, P119
[5] ALPHAND V, UNPUB
[6] BAEYER-VILLIGER MONOOXYGENASE-DEPENDENT BIOTRANSFORMATIONS - STEREOSPECIFIC HETEROATOM OXIDATIONS BY CAMPHOR-GROWN PSEUDOMONAS-PUTIDA TO PRODUCE CHIRAL SULFOXIDES
BEECHER, J
RICHARDSON, P
WILLETTS, A
[J]. BIOTECHNOLOGY LETTERS, 1994, 16 (09) : 909 - 912
[7] ASYMMETRIC OXIDATION OF 1,3-DITHIOLANES - A ROUTE TO THE OPTICAL RESOLUTION OF CARBONYL-COMPOUNDS
BORTOLINI, O
DIFURIA, F
LICINI, G
MODENA, G
ROSSI, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (51) : 6257 - 6260
[8] HIGHLY ENANTIOSELECTIVE OXIDATION OF SULFIDES MEDIATED BY A CHIRAL TITANIUM COMPLEX
BRUNEL, JM
DITER, P
DUETSCH, M
KAGAN, HB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) : 8086 - 8088
[9] EFFECTS OF SUBSTRATE STRUCTURE ON THE ENANTIOSELECTIVITY AND STEREOCHEMICAL COURSE OF SULFOXIDATION CATALYZED BY CYCLOHEXANONE MONOOXYGENASE
CARREA, G
REDIGOLO, B
RIVA, S
COLONNA, S
GAGGERO, N
BATTISTEL, E
BIANCHI, D
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (08) : 1063 - 1068
[10] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS
CARRENO, MC
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1717 - 1760

← 1 2 3 4 →