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Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester

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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

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