|
Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Agriculture / Faculty of Agriculture >
Peer-reviewed Journal Articles, etc >
Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester
This item is licensed under:Creative Commons Attribution 4.0 International
| Title: | Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
| Authors: | Tachrim, Zetryana Puteri Browse this author | | Oida, Kazuhiro Browse this author | | Ikemoto, Haruka Browse this author | | Ohashi, Fumina Browse this author | | Kurokawa, Natsumi Browse this author | | Hayashi, Kento Browse this author | | Shikanai, Mami Browse this author | | Sakihama, Yasuko Browse this author →KAKEN DB | | Hashidoko, Yasuyuki Browse this author →KAKEN DB | | Hashimoto, Makoto Browse this author →KAKEN DB |
| Keywords: | N-hydroxysuccinimide ester | | Friedel-Crafts acylation | | alpha-amino acid | | alpha-amino aryl-ketone | | racemization |
| Issue Date: | Oct-2017 |
| Publisher: | MDPI |
| Journal Title: | Molecules |
| Volume: | 22 |
| Issue: | 10 |
| Start Page: | 1748 |
| Publisher DOI: | 10.3390/molecules22101748 |
| Abstract: | Chiral N-protected alpha-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel-Crafts acylation of N-protected alpha-amino acids. One of the drawbacks of this reaction is the utilization of toxic, corrosive and moisture-sensitive acylating reagents. In peptide construction via amide bond formation, N-hydroxysuccinimide ester (OSu), which has high storage stability, can react rapidly with amino components and produces fewer side reactions, including racemization. This study reports the first synthesis and utilization of N-trifluoroacetyl (TFA)-protected alpha-amino acid-OSu as a potential acyl donor for Friedel-Crafts acylation into various arenes. The TFA-protected isoleucine derivative and its diastereomer TFA-protected allo-isoleucine derivative were investigated to check the retention of alpha-proton chirality in the Friedel-Crafts reaction. Further utilization of OSu in other branched-chain and unbranched-chain amino acids results in an adequate yield of TFA-protected alpha-amino aryl-ketone without loss of optical purity. |
| Rights: | https://creativecommons.org/licenses/by/4.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/68009 |
| Appears in Collections: | 農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
|
Submitter: 橋本 誠
|
