Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide

Ogasahara, Riku; Mae, Miyu; Matsuura, Keisuke; Yoshimura, Sota; Ishimoto, Takayoshi; Udagawa, Taro; Harada, Kazuo; Fujioka, Hiroyoshi; Kamiya, Mako; Asada, Rio; Uchiyama, Hiromasa; Tozuka, Yuichi; Akai, Shuji; Sawama, Yoshinari

doi:https://doi.org/10.1002/chem.202404204

Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide

Ogasahara, Riku; Mae, Miyu; Matsuura, Keisuke et al.

Chemistry - A European Journal, 2025, e202404204

アクセス数:22件（2025-04-10 08:35 集計）

固定URL: https://hdl.handle.net/11094/100347

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タイトル	Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide
著者	著者名 Ogasahara, Riku
	著者名 Mae, Miyu
	著者名 Matsuura, Keisuke
	著者名 Yoshimura, Sota
	NRID 1000050543435 1000050543435 著者名 Ishimoto, Takayoshi
	NRID 1000070509356 1000070509356 著者名 Udagawa, Taro
	NRID 1000050397741 1000050397741 ORCID 0000-0002-9348-1629 0000-0002-9348-1629 researchmap permalink read0204933 read0204933 Scopus Author ID 16549528100 16549528100 著者名 Harada, Kazuo
	著者名 Fujioka, Hiroyoshi
	著者名 Kamiya, Mako
	著者名 Asada, Rio
	NRID 1000060792744 1000060792744 著者名 Uchiyama, Hiromasa
	NRID 1000050312963 1000050312963 著者名 Tozuka, Yuichi
	NRID 1000060192457 1000060192457 ORCID 0000-0001-9149-8745 0000-0001-9149-8745 researchmap permalink shuji_akai shuji_akai Scopus Author ID 7006001526 7006001526 著者名 Akai, Shuji
	NRID 1000080552413 1000080552413 ORCID 0000-0002-9923-2412 0000-0002-9923-2412 researchmap permalink sawama sawama Scopus Author ID 6505798196 6505798196 著者名 Sawama, Yoshinari
キーワード等	Deuterium oxide
	H/D exchange reaction
	Photocatalytic reaction
	Polyethylene glycol
内容	Ogasahara R., Mae M., Matsuura K., et al. Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide. Chemistry - A European Journal , (2025); https://doi.org/10.1002/chem.202404204.
抄録	Deuterated molecules are of growing interest because of the specific characteristics of deuterium, such as stronger C−D bonds being stronger than C−H bonds. Polyethylene glycols (PEGs) are widely utilized in scientific fields (e. g., drug discovery and material sciences) as linkers and for the improvement of various properties (solubility in water, stability, etc.) of mother compounds. Therefore, deuterated PEGs can be used as novel tools for drug discovery. Although the H/D exchange reaction (deuteration) is a powerful and straightforward method to produce deuterated compounds, the deuteration of PEGs bearing many unactivated C(sp3)−H bonds has not been developed. Herein, we report the photocatalytic deuteration of multiple sites of PEGs using tetra-n-butylammonium decatungstate (TBADT) and D2O as an inexpensive deuterium source. This deuteration can be adapted to PEG derivatives bearing various substituents ((hetero)aryl, benzoyl, alkyl, etc.). The deuteration efficiencies of the α-oxy C(sp3)−H bonds at the terminal positions of the PEGs were strongly influenced by the substituents. These reactivities were elucidated by density functional theory calculations of the reaction barriers towards the formation of radical intermediates, induced by the excited state of TBADT and the PEG substrate. In addition, the applicability of deuterated PEGs to internal standard experiments and Raman spectroscopy was demonstrated.
出版者	John Wiley and Sons Inc
収録物名	Chemistry - A European Journal
ページ	e202404204
刊行年月	2025-01-07
言語	英語
ハンドルURL	https://hdl.handle.net/11094/100347
PISSN	09476539
eISSN	15213765
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1002/chem.202404204
アクセス権	open access
権利情報	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
出版タイプ	Version of Record
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCTERMS.bibliographicCitation	Chemistry - A European Journal. 2025, p. e202404204
DC.title	Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide
DC.creator	Ogasahara, Riku
	Mae, Miyu
	Matsuura, Keisuke
	Yoshimura, Sota
	Ishimoto, Takayoshi
	Udagawa, Taro
	Harada, Kazuo
	Fujioka, Hiroyoshi
	Kamiya, Mako
	Asada, Rio
	Uchiyama, Hiromasa
	Tozuka, Yuichi
	Akai, Shuji
	Sawama, Yoshinari
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	英語
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2025-01-07
DC.identifier	https://doi.org/10.1002/chem.202404204
DC.subject	Deuterium oxide
	H/D exchange reaction
	Photocatalytic reaction
	Polyethylene glycol
DC.description	Ogasahara R., Mae M., Matsuura K., et al. Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide. Chemistry - A European Journal , (2025); https://doi.org/10.1002/chem.202404204.
DCTERMS.abstract	Deuterated molecules are of growing interest because of the specific characteristics of deuterium, such as stronger C−D bonds being stronger than C−H bonds. Polyethylene glycols (PEGs) are widely utilized in scientific fields (e. g., drug discovery and material sciences) as linkers and for the improvement of various properties (solubility in water, stability, etc.) of mother compounds. Therefore, deuterated PEGs can be used as novel tools for drug discovery. Although the H/D exchange reaction (deuteration) is a powerful and straightforward method to produce deuterated compounds, the deuteration of PEGs bearing many unactivated C(sp3)−H bonds has not been developed. Herein, we report the photocatalytic deuteration of multiple sites of PEGs using tetra-n-butylammonium decatungstate (TBADT) and D2O as an inexpensive deuterium source. This deuteration can be adapted to PEG derivatives bearing various substituents ((hetero)aryl, benzoyl, alkyl, etc.). The deuteration efficiencies of the α-oxy C(sp3)−H bonds at the terminal positions of the PEGs were strongly influenced by the substituents. These reactivities were elucidated by density functional theory calculations of the reaction barriers towards the formation of radical intermediates, induced by the excited state of TBADT and the PEG substrate. In addition, the applicability of deuterated PEGs to internal standard experiments and Raman spectroscopy was demonstrated.
DC.rights	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
DC.format	100347
citation_title	Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide
citation_author	Ogasahara, Riku
	Mae, Miyu
	Matsuura, Keisuke
	Yoshimura, Sota
	Ishimoto, Takayoshi
	Udagawa, Taro
	Harada, Kazuo
	Fujioka, Hiroyoshi
	Kamiya, Mako
	Asada, Rio
	Uchiyama, Hiromasa
	Tozuka, Yuichi
	Akai, Shuji
	Sawama, Yoshinari
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2025-01-07
citation_journal_title	Chemistry - A European Journal
citation_firstpage	e202404204
citation_doi	https://doi.org/10.1002/chem.202404204
citation_public_url	https://hdl.handle.net/11094/100347

Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide

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