α Hydroxylation of Carboxylic Acids with Molecular Oxygen Catalyzed by the α Oxidase of Peas (<i>Pisum </i><i>s</i><i>ativum</i>): A Novel Biocatalytic Synthesis of Enantiomerically Pure (<i>R</i>)-2-Hydroxy Acids
作者:Waldemar Adam、Wilhelm Boland、Jenny Hartmann-Schreier、Hans-Ulrich Humpf、Michael Lazarus、Alexander Saffert、Chantu R. Saha-Möller、Peter Schreier
DOI:10.1021/ja981252r
日期:1998.11.1
the α oxidation of saturated, unsaturated, and heteroatom-containing (oxygen, sulfur) carboxylic acids 1 by the enzyme extract of peas (Pisum sativum) indicate that this biotransformation proceeds highly enantioselectively. For the first time, the synthesis of optically pure 2-hydroxy acids 2 has been achieved on the semipreparative scale (1 mmol) by α hydroxylation of long-chain carboxylic acids with
豌豆 (Pisum sativum) 的酶提取物对饱和、不饱和和含杂原子(氧、硫)羧酸 1 进行 α 氧化的底物选择性表明,这种生物转化具有高度的对映选择性。在豌豆的α氧化酶的催化下,通过长链羧酸与分子氧的α羟基化,首次在半制备规模(1 mmol)上合成了光学纯的2-羟基酸2。对于链中带有硫原子的衍生物,没有观察到亚砜化。官能团(碳双键和三键、氧和硫原子)必须距离羧酸基团至少三个碳原子才能实现有效的不对称羟基化。2-羟基酸 2 的绝对构型是通过将气相色谱数据与真实参考化合物的数据进行比较并通过应用激子耦合圆二色性 (ECCD) 方法来确定的。这种前所未有的不对称...