First asymmetric epoxidation catalysed by cyclohexanone monooxygenase

被引：57

作者：

Colonna, S

Gaggero, N

Carrea, G

Ottolina, G

Pasta, P

Zambianchi, F

机构：

[1] Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

[2] CNR, Ist Biocatalisi & Riconoscimento Mol, I-20131 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(02)00029-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of a totally enantioselective epoxidation mediated by cyclohexanone monooxygenase for a model compound related to fosfomycin is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1797 / 1799

页数：3

共 12 条

[1]

[Anonymous], UNPUB

[2] MONOOXYGEN DONATION POTENTIAL OF 4A-HYDROPEROXYFLAVINS AS COMPARED WITH THOSE OF A PERCARBOXYLIC ACID AND OTHER HYDROPEROXIDES - MONOOXYGEN DONATION TO OLEFIN, TERTIARY AMINE, ALKYL SULFIDE, AND IODIDE-ION [J].

BRUICE, TC ;

NOAR, JB ;

BALL, SS ;

VENKATARAM, UV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2452-2463

[3] Enantioselective oxidation of sulfides to sulfoxides catalysed by bacterial cyclohexanone monooxygenases [J].

Colonna, S ;

Gaggero, N ;

Pasta, P ;

Ottolina, G .

CHEMICAL COMMUNICATIONS, 1996, (20) :2303-2307

[4] A new enzymatic enantioselective synthesis of dialkyl sulfoxides catalysed by monooxygenases [J].

Colonna, S ;

Gaggero, N ;

Carrea, G ;

Pasta, P .

CHEMICAL COMMUNICATIONS, 1997, (05) :439-440

[5] ENANTIOSELECTIVE OXIDATION OF 1,3-DITHIOACETALS CATALYZED BY CYCLOHEXANONE MONOOXYGENASE [J].

COLONNA, S ;

GAGGERO, N ;

BERTINOTTI, A ;

CARREA, G ;

PASTA, P ;

BERNARDI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) :1123-1124

[6] Oxidation of organic cyclic sulfites to sulfates: a new reaction catalyzed by cyclohexanone monooxygenase [J].

Colonna, S ;

Gaggero, N ;

Carrea, G ;

Pasta, P .

CHEMICAL COMMUNICATIONS, 1998, (03) :415-416

[7] Large scale production of cyclohexanone monooxygenase from Escherichia coli TOP10 pQR239 [J].

Doig, SD ;

O'Sullivan, LM ;

Patel, S ;

Ward, JM ;

Woodley, JM .

ENZYME AND MICROBIAL TECHNOLOGY, 2001, 28 (2-3) :265-274

[8] Protein purification and function assignment of the epoxidase catalyzing the formation of fosfomycin [J].

Liu, PH ;

Murakami, K ;

Seki, T ;

He, XM ;

Yeung, SM ;

Kuzuyama, T ;

Seto, H ;

Liu, HW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4619-4620

[9] First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase [J].

Ottolina, G ;

Bianchi, S ;

Belloni, B ;

Carrea, G ;

Danieli, B .

TETRAHEDRON LETTERS, 1999, 40 (48) :8483-8486

[10] Mechanistic studies of cyclohexanone monooxygenase: Chemical properties of intermediates involved in catalysis [J].

Sheng, DW ;

Ballou, DP ;

Massey, V .

BIOCHEMISTRY, 2001, 40 (37) :11156-11167

← 1 2 →