A proposal for the origin of stereoselectivity in enzyme catalysed Baeyer-Villiger reactions

被引：22

作者：

Kelly, DR

机构：

[1] Department of Chemistry, University of Wales, College of Cardiff, Cardiff, CF1 3TB, Wales

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 04期

关键词：

D O I：

10.1016/0957-4166(96)00120-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The mechanism for flavoenzyme catalysed Baeyer-Villiger ring expansions is proposed to proceed via a 4-hydroxy-1,2,5-trioxane adduct formed from the ketone and a flavin hydroperoxide. In consequence the enantioselectivity of the transformation is dictated by which side of the flavin cofactor reacts with the ketone. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1149 / 1152

页数：4

共 20 条

[1] The Nomen clature of superoxides and the super oxides od aldehydes [J].

Baeyer, A ;

Villiger, V .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1900, 33 :2479-2487

[2]

Baeyer A., 1899, BER DTSCH CHEM GES, V32, P3625, DOI [10.1002/cber.189903203151, DOI 10.1002/CBER.189903203151]

[3] 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

[4] CONFORMATIONALLY RESTRICTED CRIEGEE INTERMEDIATES - EVIDENCE FOR FORMATION AND STEREOELECTRONICALLY CONTROLLED FRAGMENTATION [J].

CHANDRASEKHAR, S ;

ROY, CD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (10) :2141-2143

[5]

DESLONCHAMPS P, 1983, STEREOELECTRONIC EFF, P313

[6] PURIFICATION AND PROPERTIES OF CYCLOHEXANONE OXYGENASE FROM NOCARDIA-GLOBERULA CL1 AND ACINETOBACTER NCIB-9871 [J].

DONOGHUE, NA ;

NORRIS, DB ;

TRUDGILL, PW .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1976, 63 (01) :175-192

[7] BIOLOGICAL BAEYER-VILLIGER OXIDATION OF SOME MONOCYCLIC AND BICYCLIC KETONES USING MONOOXYGENASES FROM ACINETOBACTER-CALCOACETICUS NCIMB-9871 AND PSEUDOMONAS-PUTIDA NCIMB-10007 [J].

GAGNON, R ;

GROGAN, G ;

LEVITT, MS ;

ROBERTS, SM ;

WAN, PWH ;

WILLETTS, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18) :2537-2543

[8] MODEL FOR THE FUNCTIONAL ACTIVE-SITE OF BAEYER-VILLIGERASES - X-RAY CRYSTAL DATA FOR (1S,2R,5R,8S,1'R)-8-ENDO-BENZOYLOXY-N-(1'-PHENYLETHYL)BICYCLO[3.3.0]OCTANE-2-ENDO-CARBOXAMIDE [J].

KELLY, DR ;

KNOWLES, CJ ;

MAHDI, JG ;

WRIGHT, MA ;

TAYLOR, IN ;

HIBBS, DE ;

HURSTHOUSE, MB ;

MISHAL, AK ;

ROBERTS, SM ;

WAN, PWH ;

GROGAN, G ;

WILLETTS, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (16) :2057-2066

[9]

Krow G.R., 1993, ORGANIC REACTIONS, V43, P251, DOI DOI 10.1002/0471264180.OR043.03

[10] LIPASE-CATALYZED BAEYER-VILLIGER REACTIONS [J].

LEMOULT, SC ;

RICHARDSON, PF ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (02) :89-91

← 1 2 →