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

Tachrim, Zetryana Puteri; Oida, Kazuhiro; Ikemoto, Haruka; Ohashi, Fumina; Kurokawa, Natsumi; Hayashi, Kento; Shikanai, Mami; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto

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

Tachrim, Zetryana Puteri; Oida, Kazuhiro; Ikemoto, Haruka et al.

Molecules, 2017, 22(10), 1748

Permalink : https://hdl.handle.net/2115/68009

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アクセス権	open access
URI	https://hdl.handle.net/2115/68009
タイトル	Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester
著者	Tachrim, Zetryana Puteri ; Oida, Kazuhiro ; Ikemoto, Haruka ; Ohashi, Fumina ; Kurokawa, Natsumi ; Hayashi, Kento ; Shikanai, Mami ; Sakihama, Yasuko ; Hashidoko, Yasuyuki ; Hashimoto, Makoto
著者名 Tachrim, Zetryana Puteri
著者名 Oida, Kazuhiro
著者名 Ikemoto, Haruka
著者名 Ohashi, Fumina
著者名 Kurokawa, Natsumi
著者名 Hayashi, Kento
著者名 Shikanai, Mami
e-Rad_Researcher 10344491 著者名 Sakihama, Yasuko
e-Rad_Researcher 40281795 著者名 Hashidoko, Yasuyuki
e-Rad_Researcher 90292094 著者名 Hashimoto, Makoto
言語	英語
キーワード	N-hydroxysuccinimide ester
	Friedel-Crafts acylation
	alpha-amino acid
	alpha-amino aryl-ketone
	racemization
発行日	2017-10
出版者	MDPI
収録物名	Molecules
巻(号)	22(10)
ページ	1748
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Version of Record
権利情報	Creative Commons Attribution 4.0 International
PISSN	1420-3049
関連情報 (isIdenticalTo)	出版社版DOI https://doi.org/10.3390/molecules22101748