Enzymatic resolution of chiral 2-hydroxy carboxylic acids by enantioselective oxidation with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea)
Enzymatic resolution of chiral 2-hydroxy carboxylic acids by enantioselective oxidation with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea)
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DOI：
10.1021/jo971298n
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发表时间：
1997-10-31
影响因子：
3.6
通讯作者：
Schreier, P
中科院分区：
文献类型：
--
作者：
Adam, W;Lazarus, M;Schreier, P
从菠菜（Spinacia oleracea）中提取的乙醇酸氧化酶在分子氧催化下将各种饱和和不饱和脂肪衍生物的2-羟基酸1氧化为2-氧酸2，显示出高度的对映选择性。因此，乙醇酸氧化酶催化的动力学分解为制备对映体纯(R)-2-羟基酸提供了一种方便的生物催化方法。采用激子耦合圆二色性方法（ECCD）对其双色性2-萘酸9-甲基基衍生物3b进行了旋光度测量和文献数据的比较，确定了(R)-2-羟基酸Ib的绝对构型。这些结果表明ECCD方法是一种方便的用于2-羟基酸构型分配的微尺度色光工具。
The enzymatic oxidation of a variety of saturated and unsaturated aliphatic derivatives of racemic 2-hydroxy acids 1 to their 2-oxo acids 2 with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) was shown to proceed highly enantioselectively. Thus, the glycolate oxidase-catalyzed kinetic resolution provides a convenient biocatalytic method for the preparation of enantiomerically pure (R)-2-hydroxy acids. The absolute configuration of tbe (R)-2-hydroxy acid Ib was assigned by comparison of the measured optical rotation value with that of the literature data and by application of the exciton-coupled circular dichroism method (ECCD) on its bichromophoric 2-naphthoate 9-methylanthryl derivative 3b. These results establish the ECCD method as a convenient microscale chirooptic tool for the configurational assignment of 2-hydroxy acids.