Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide

Takahiro Moriyama; Daiki Mizukami; Makoto Yoritate; Kazuteru Usui; Daisuke Takahashi; Eisuke Ota; Mikiko Sodeoka; Tadashi Ueda; Satoru Karasawa; Go Hirai

doi:10.1002/chem.202103925

Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide

Takahiro Moriyama, Daiki Mizukami, Makoto Yoritate, Kazuteru Usui^*, Daisuke Takahashi, Eisuke Ota, Mikiko Sodeoka, Tadashi Ueda, Satoru Karasawa, Go Hirai

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Minimalist photo-reactive probes, which consist of a photo-reactive group and a tag for detection of target proteins, are useful tools in chemical biology. Although several diazirine-based and aryl azide-based minimalist probes are available, no keto-based minimalist probe has yet been reported. Here we describe minimalist probes based on a 2-thienyl-substituted α-ketoamide bearing an alkyne group on the thiophene ring. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.

Original language	English
Article number	e202103925
Journal	Chemistry - A European Journal
Volume	28
Issue number	11
DOIs	https://doi.org/10.1002/chem.202103925
Publication status	Published - 2022 Feb 19
Externally published	Yes

Keywords

alkynes
photo-affinity labeling
spin density
thiophenes
α-ketoamides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202103925

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title = "Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide",

abstract = "Minimalist photo-reactive probes, which consist of a photo-reactive group and a tag for detection of target proteins, are useful tools in chemical biology. Although several diazirine-based and aryl azide-based minimalist probes are available, no keto-based minimalist probe has yet been reported. Here we describe minimalist probes based on a 2-thienyl-substituted α-ketoamide bearing an alkyne group on the thiophene ring. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.",

keywords = "alkynes, photo-affinity labeling, spin density, thiophenes, α-ketoamides",

author = "Takahiro Moriyama and Daiki Mizukami and Makoto Yoritate and Kazuteru Usui and Daisuke Takahashi and Eisuke Ota and Mikiko Sodeoka and Tadashi Ueda and Satoru Karasawa and Go Hirai",

note = "Funding Information: This study was partially supported by PRIME and the Platform Project for Supporting Drug Discovery and Life Science Research (BINDS) from the Japan Agency for Medical Research and Development, AMED, the JSPS KAKENHI (grants no. 21K19053, 21H02070, and 20K15957), and the Sumitomo Foundation. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = feb,

day = "19",

doi = "10.1002/chem.202103925",

language = "English",

volume = "28",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide

AU - Moriyama, Takahiro

AU - Mizukami, Daiki

AU - Yoritate, Makoto

AU - Usui, Kazuteru

AU - Takahashi, Daisuke

AU - Ota, Eisuke

AU - Sodeoka, Mikiko

AU - Ueda, Tadashi

AU - Karasawa, Satoru

AU - Hirai, Go

N1 - Funding Information: This study was partially supported by PRIME and the Platform Project for Supporting Drug Discovery and Life Science Research (BINDS) from the Japan Agency for Medical Research and Development, AMED, the JSPS KAKENHI (grants no. 21K19053, 21H02070, and 20K15957), and the Sumitomo Foundation. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/2/19

Y1 - 2022/2/19

N2 - Minimalist photo-reactive probes, which consist of a photo-reactive group and a tag for detection of target proteins, are useful tools in chemical biology. Although several diazirine-based and aryl azide-based minimalist probes are available, no keto-based minimalist probe has yet been reported. Here we describe minimalist probes based on a 2-thienyl-substituted α-ketoamide bearing an alkyne group on the thiophene ring. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.

AB - Minimalist photo-reactive probes, which consist of a photo-reactive group and a tag for detection of target proteins, are useful tools in chemical biology. Although several diazirine-based and aryl azide-based minimalist probes are available, no keto-based minimalist probe has yet been reported. Here we describe minimalist probes based on a 2-thienyl-substituted α-ketoamide bearing an alkyne group on the thiophene ring. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.

KW - alkynes

KW - photo-affinity labeling

KW - spin density

KW - thiophenes

KW - α-ketoamides

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DO - 10.1002/chem.202103925

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SN - 0947-6539

VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 11

M1 - e202103925

ER -

Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide

Abstract

Keywords

ASJC Scopus subject areas

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