Enantioselective N-acetylation of 2-phenylglycine by an unusual N-acetyltransferase from Chryseobacterium sp.
Enantioselective N-acetylation of 2-phenylglycine by an unusual N-acetyltransferase from Chryseobacterium sp.
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通过来自 Chryseobacter sp. 的一种不寻常的 N-乙酰转移酶对 2-苯基甘氨酸进行对映选择性 N-乙酰化。
DOI：
10.1007/s10529-013-1172-z
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发表时间：
2013
影响因子：
2.7
通讯作者：
Shinji Takenaka
中科院分区：
文献类型：
--
作者：
Kenko Azuma;Hokuto Ohtsuka;Yurie Koga;Chikako Naito;Hiroshi Murakami;and Hirofumi Aiba.;Shinji Takenaka
用于合成半合成抗生素和农药的福特-2-苯甘氨酸的需求量不断增加。分离出金黄杆菌属（Chryseobacteriumsp.）在最佳培养条件下，以50%的摩尔产率和> 99.5%的对映体过量将外消旋形式的1 -2-苯基甘氨酸选择性地转化为（2S）-2-乙酰胺-2-苯基乙酸，从而导致99%纯的2-苯基甘氨酸保留在培养物中。对映体选择性N-乙酰化反应由乙酰辅酶A依赖性N-乙酰转移酶催化，该转移酶的合成由byl-2-苯基甘氨酸诱导。该酶不同于以前报道的细菌arylamineN-乙酰转移酶的分子量和底物特异性。该酶与底物1 -2-苯甘氨酸、d-2-苯甘氨酸、2-（2-氯苯基）甘氨酸和5-氨基水杨酸（芳香胺N-乙酰转移酶的良好底物）的相对活性比分别为100：0：56.9：5.49。本文报道的N-乙酰基转移酶产生菌的生物转化为d，l-2-苯甘氨酸的酶法拆分提供了一条新的制备途径。
The demand ford-2-phenylglycine used to synthesize semisynthetic antibiotics and pesticides is increasing. We have isolated aChryseobacteriumsp. that selectively transformed thel-form of racemicd,l-2-phenylglycine to (2S)-2-acetylamide-2-phenylacetic acid with a molar yield of 50 % and an enantiomer excess of >99.5 % under optimal culture conditions, consequently resulting in 99 % pured-2-phenylglycine remaining in the culture. The enantioselectiveN-acetylation was catalyzed by an acetyl-CoA-dependentN-acetyltransferase whose synthesis was induced byl-2-phenylglycine. The enzyme differed from previously reported bacterial arylamineN-acetyltransferases in molecular mass and substrate specificity. The relative activity ratio of the enzyme with the substratesl-2-phenylglycine,d-2-phenylglycine, 2-(2-chlorophenyl)glycine, and 5-aminosalicylic acid (a good substrate of arylamineN-acetyltransferase) was 100:0:56.9:5.49, respectively. The biotransformation by theN-acetyltransferase-producing bacterium reported here could constitute a new preparative route for the enzymatic resolution ofd,l-2-phenylglycine.