Stereospecific sulfoxidation by toluene and naphthalene dioxygenases.

Stereospecific sulfoxidation by toluene and naphthalene dioxygenases.
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甲苯和萘双加氧酶的立体定向磺化氧化。

DOI:
10.1006/bbrc.1995.1928
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发表时间:
1995
期刊:
Biochemical and biophysical research communications.
影响因子:
--
通讯作者:
Gibson,DT
Gibson,DT
中科院分区:
--
文献类型:
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作者:
Lee,K;Brand,JM;Gibson,DT

文献摘要

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研究了甲苯双加氧酶和萘双加氧酶对芳基烷基硫醚的磺化氧化反应,结果表明萘双加氧酶生成的亚砜具有高的对映体纯度,而甲苯双加氧酶生成的亚砜具有不同的对映体纯度,这取决于苯环上的对位取代基。萘双加氧酶的氧吸收实验表明,反应速率和氧掺入程度受芳基和烷基取代基的影响。18 O2-掺入实验表明,甲苯双加氧酶和萘双加氧酶形成的甲基苯基亚砜的氧原子完全来自O2。伴随的研究表明,氯过氧化物酶产生单一的(R)-亚砜(>98%对映体过量)从芳基烷基硫化物在本研究中检查。
Studies on the sulfoxidation of aryl alkyl sulfides by purified toluene dioxygenase and naphthalene dioxygenase showed that naphthalene dioxygenase produces sulfoxides of (S) absolute configuration in high enantiomeric purity while those formed by toluene dioxygenase are of variable enantiomeric purity depending on the p-substituents on the benzene ring. Oxygen uptake experiments with naphthalene dioxygenase showed that the reaction rate and degree of oxygen incorporation are affected by both aryl and alkyl substituents.18O2-Incorporation experiments showed that the oxygen atom of methyl phenyl sulfoxide formed by toluene dioxygenase and naphthalene dioxygenase is derived exclusively from O2. Accompanying studies showed that chloroperoxidase produces single (R)-sulfoxides (>98% enantiomeric excess) from the aryl alkyl sulfides examined in the present study.