| 酶促-化学法合成(R)-N-苄基吗啉-3-酮-2-乙酰(4-脒基)苄胺 |
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| 引用本文： | 叶海朋,钱学启,刘博凯,吴起,林贤福. 酶促-化学法合成(R)-N-苄基吗啉-3-酮-2-乙酰(4-脒基)苄胺[J]. 浙江大学学报(理学版), 2011, 38(1): 63-67. DOI: 10.3785/j.issn.1008-9497.2011.01.016 |
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| 作者姓名： | 叶海朋 钱学启 刘博凯 吴起 林贤福 |
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| 作者单位： | 浙江大学,化学系,浙江,杭州,310027 |
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| 基金项目： | 手性吗啉酮类凝血酶抑制剂的酶/离子液催化绿色合成技术开发，浙江省绿色化工重大专项 |
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| 摘 要： | 报道了一种酶促-化学法合成光学纯吗啉酮凝血酶抑制剂的新途径.以马来酸酐和氨基醇为起始原料,一锅法合成N-苄基吗啉-3-酮-2-乙酸甲酯;再用脂肪酶CAL-B在甲基叔丁基醚/水（体积分数=1/9）混合溶剂中将其选择性水解,制备光学纯（R）-N-苄基吗啉-3-酮-2-乙酸;经过酰胺化、还原/胺解,得到（R）-N-苄基吗啉-3-酮-2-乙酰（4-脒基）苄胺;所得化合物结构经IR,1H NMR,13C NMR表征确证.文中还讨论了酶源、溶剂、含水量、反应时间等因素对水解拆分的影响.
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| 关 键 词： | 酶促-化学法合成 N-苄基吗啉-3-酮 脂肪酶 凝血酶抑制剂 |
Chemo-enzymatic synthesis of N-(4-(Amino(imino)-methyl)benzyl)-2-((R)-4-benzyl-3-oxo-morpholin-2-yl)-acetamide |
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| YE Hai-peng,QIAN Xue-qi,LIU Bo-kai,WU Qi,LIN Xian-fu. Chemo-enzymatic synthesis of N-(4-(Amino(imino)-methyl)benzyl)-2-((R)-4-benzyl-3-oxo-morpholin-2-yl)-acetamide[J]. Journal of Zhejiang University(Sciences Edition), 2011, 38(1): 63-67. DOI: 10.3785/j.issn.1008-9497.2011.01.016 |
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| Authors: | YE Hai-peng QIAN Xue-qi LIU Bo-kai WU Qi LIN Xian-fu |
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| Affiliation: | YE Hai-peng,QIAN Xue-qi,LIU Bo-kai,WU Qi,LIN Xian-fu(Department of Chemistry,Zhejiang University,Hangzhou 310027,China) |
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| Abstract: | A new synthetic method of thrombin inhibitor based on morpholinone was accomplished by a chemoenzymatic approach.Racemic(4-Benzyl-3-oxo-morpholin-2-yl)-acetic acid methyl ester((R)/(S)-1) was firstly synthesized in one-pot.(R)-2 was obtained from hydrolysis of racemic 1 by CAL-B with a high enantiomeric excess(ee%=90.90) in the mixture solvent of TBME/H2O(V/V=1/9).Objective(R)-4 was synthesized by amidation and reduction/aminolysis.The structures of the title compounds were characterized by IR,1H NMR,13C NM... |
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| Keywords: | chemo-enzymatic synthesis 4-benzyl-3-oxo-morpholin lipase thrombin inhibitor |
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