朱炜,杨可武,姜玄珍.化学酶法合成光学纯亮氨酸[J].分子催化,2005,(5):399-402
化学酶法合成光学纯亮氨酸
Chemoenzymatic Synthesis of Enantiomerically Pure Leucine
投稿时间:2005-03-07  修订日期:2005-04-27
DOI:
中文关键词:  化学酶法合成  酰胺羰基化  光学纯亮氨酸  酶水解
英文关键词:Chemoenzymatic synthesis  Amidocarbonylation  Enantiomerically pure leucine  Enzymatic hydrolysis
基金项目:中国科学院资助项目
朱炜  杨可武  姜玄珍
浙江大学玉泉校区化学系,浙江杭州310027
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中文摘要:
      用化学酶法合成L-亮氨酸,先在PdCl2/PPh3/LiBr/H2SO4催化体系作用下,异戊醛酰胺羰基化合成消旋的N-乙酰基亮氨酸;然后在酰基转移酶催化下水解,得到L-亮氨酸和N-乙酰基-D-亮氨酸.文中对酰胺羰基化反应条件进行了优化,分离得到消旋N-乙酰基亮氨酸产率为66.4%.经酶对映选择地水解后得L-亮氨酸,产率为41%,产物L-亮氨酸经衍生化后由气相色谱测定其光学纯度达99%ee.
英文摘要:
      In this study enantiomerically L-leucine was prepared by chemoenzymatic synthesis.In the first step of the reaction sequence the racemic N-acetylleucine was prepared by amidocarbonylation from isovaleraldehyde,acetamide and carbon monoxide in the presence of PdCl_2/PPh_3/LiBr/H_2SO_4 catalyst system.Subsequently L-leucine andD-N-acetylleucine were obtained by the acylase-catalyzed hydrolysis.The amidocarbonylation reaction conditions were optimized and 66.4% isolated yield of racemic N-acetylleucine were obtained.L-leucine was obtained from the enzymatic enantioselective hydrolysis of racemic N-acetylleucine in a yield of 41%,and its derivative enantiomeric purity determined by G.C was 99% ee.
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