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Synthesis of chiral N-trifluoroacetyl-methionine derivatives and applying them as acyl donors for Friedel-Crafts acylation

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Title: Synthesis of chiral N-trifluoroacetyl-methionine derivatives and applying them as acyl donors for Friedel-Crafts acylation
Authors: Kurokawa, Natsumi Browse this author
Tokoro, Yurika Browse this author
Tachrim, Zetryana Puteri Browse this author
Wakasa, Haruna 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: Trifluoroacetamide
alpha-amino acid
N-hydroxysuccinimide ester
Friedel-Crafts acylation
alpha-amino phenyl ketone
Issue Date: 20-Jan-2019
Publisher: ARKAT USA, INC.
Journal Title: Arkivoc
Volume: 5
Start Page: 42
End Page: 49
Publisher DOI: 10.24820/ark.5550190.p010.815
Abstract: A chiral N-protected alpha-amino acid N-hydroxysuccinimide ester (OSu) is a common useful reagent for peptide bond formation. Recently, N-trifluoroacetyl (TFA) alpha-amino acid OSu esters have been reported as acyl donors for Frieldel-Crafts reactions to synthesize chiral alpha-amino phenyl ketones retaining the configurations of the starting alpha-amino acids. There are few reports for chiral TFA protected methionine, which has methylthioethyl structure in the side-chain of the alpha-amino acid. The detailed synthesis of chiral TFA-Met-OSu and its application as an acyl donor for Friedel-Crafts acylation is reported.
Rights: https://creativecommons.org/licenses/by-nc/4.0/
Type: article
URI: http://hdl.handle.net/2115/75685
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)

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