Tailor-Made alpha-Amino Acids in the Pharmaceutical Industry: Synthetic Approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA)
文献类型：期刊论文
| 作者 | Sato, Tatsunori2; Izawa, Kunisuke2; Luis Acena, Jose1,3; Liu, Hong4 ; Soloshonok, Vadim A.1,5
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| 刊名 | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2016-06 |
| 期号 | 16页码:2757-2774 |
| 关键词 | Asymmetric synthesis Amino acids Medicinal chemistry Drug design Antiviral agents |
| ISSN号 | 1434-193X |
| DOI | 10.1002/ejoc.201600112 |
| 文献子类 | Review |
| 英文摘要 | (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic acid (vinyl-ACCA) is the essential pharmacophoric unit in a new generation of highly potent hepatitis C virus (HCV) NS3/4A protease inhibitors. Currently, there are over a dozen drugs under development that use the special properties of this highly sterically constrained tailor-made amino acid, underscoring the extremely high demand for the asymmetric synthesis of (1R,2S)-vinyl-ACCA. This work presents a comprehensive overview of methods that have been developed to date for the preparation of (1R,2S)-vinyl-ACCA and its optical isomers. The presented data are grouped in three sections based on the biocatalytic, catalytic, and stoichiometric source of chirality. Aspects of operational convenience, practicality, and scalability are critically discussed. |
| WOS关键词 | MICHAEL ADDITION-REACTIONS ; NUCLEOPHILIC GLYCINE EQUIVALENTS ; DYNAMIC KINETIC RESOLUTION ; VIRUS NS3/4A PROTEASE ; CHIRAL NI(II) COMPLEX ; OPERATIONALLY CONVENIENT CONDITIONS ; SUBSTITUTED PYROGLUTAMIC ACIDS ; PRACTICAL ASYMMETRIC-SYNTHESIS ; CATALYZED TANDEM ALKYLATION ; ENANTIOMERICALLY PURE FORM |
| 资助项目 | Basque Foundation for Science (IKERBASQUE)[00000000] ; Basque Government[00000000] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000379753900002 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276011]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Sato, Tatsunori; Soloshonok, Vadim A. |
| 作者单位 | 1.Univ Basque Country UPV EHU, Dept Organ Chem 1, Fac Chem, Paseo Manuel Lardizabal 3, San Sebastian, Spain; 2.Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan; 3.Univ Autonoma Madrid, Dept Organ Chem, E-28049 Madrid, Spain; 4.Chinese Acad Sci, Key Lab Receptor Res, Shanghai Inst Mat Med, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China; 5.Basque Fdn Sci, Ikerbasque, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain |
| 推荐引用方式 GB/T 7714 | Sato, Tatsunori,Izawa, Kunisuke,Luis Acena, Jose,et al. Tailor-Made alpha-Amino Acids in the Pharmaceutical Industry: Synthetic Approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA)[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2016(16):2757-2774. |
| APA | Sato, Tatsunori,Izawa, Kunisuke,Luis Acena, Jose,Liu, Hong,&Soloshonok, Vadim A..(2016).Tailor-Made alpha-Amino Acids in the Pharmaceutical Industry: Synthetic Approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA).EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(16),2757-2774. |
| MLA | Sato, Tatsunori,et al."Tailor-Made alpha-Amino Acids in the Pharmaceutical Industry: Synthetic Approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA)".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .16(2016):2757-2774. |
入库方式： OAI收割
来源：上海药物研究所
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