Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites

被引：15

作者：

Boyd, Derek R. ^{[1
]}

Sharma, Narain D. ^{[1
]}

Stevenson, Paul J. ^{[1
]}

Blain, Marine ^{[2
,3
]}

McRoberts, Colin ^{[2
]}

Hamilton, John T. G. ^{[2
,4
]}

Argudo, Jose M. ^{[4
]}

Mundi, Harpinder ^{[4
]}

Kulakov, Leonid A. ^{[4
]}

Allen, Christopher C. R. ^{[4
]}

机构：

[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland

[2] Agri Food & Biosiences Inst No Ireland, Belfast BT9 5PX, Antrim, North Ireland

[3] Ensicaen, F-14050 Caen, France

[4] Queens Univ Belfast, Sch Biol Sci, Belfast BT9 5AG, Antrim, North Ireland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 05期

关键词：

PSEUDOMONAS-PUTIDA; DIHYDRODIOL METABOLITES; ABSOLUTE-CONFIGURATION; NAPHTHALENE DIOXYGENASE; BACTERIAL METABOLISM; CIRCULAR-DICHROISM; TOLUENE; DEGRADATION; BENZENE; ENZYME;

D O I：

10.1039/c0ob00894j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis-Dihydroxylation of meta-substituted phenol (m-phenol) substrates, to yield the corresponding cyclohexenone cis-diol metabolites, was catalysed by arene dioxygenases present in mutant and recombinant bacterial strains. The presence of cyclohexenone cis-diol metabolites and several of their cyclohexene and cyclohexane cis-triol derivatives was detected by LC-TOFMS analysis and confirmed by NMR spectroscopy. Structural and stereochemical analyses of chiral ketodiol bioproducts, was carried out using NMR and CD spectroscopy and stereochemical correlation methods. The formation of enantiopure cyclohexenone cis-diol metabolites is discussed in the context of postulated binding interactions of the m-phenol substrates at the active site of toluene dioxygenase (TDO).

引用

页码：1479 / 1490

页数：12

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