Photo-induced imine reduction by a photoredox biocatalyst consisting of a pentapeptide and a Ru bipyridine terpyridine complex

Kano, Ryusei; Oohora, Koji; Hayashi, Takashi

Journal of Inorganic Biochemistry, 2024, 259, 112657

Number of Access:389（2025-07-27 21:16 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/98160

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Title
Photo-induced imine reduction by a photoredox biocatalyst consisting of a pentapeptide and a Ru bipyridine terpyridine complex
Creator
CreatorName
Kano, Ryusei
NRID
1000010631202 1000010631202
ORCID
0000-0003-1155-6824 0000-0003-1155-6824
researchmap permalink
Oohora Oohora
Scopus Author ID
57200199412 57200199412
CreatorName
Oohora, Koji
NRID
1000020222226 1000020222226
ORCID
0000-0002-2215-935X 0000-0002-2215-935X
researchmap permalink
20190602_Sun 20190602_Sun
Scopus Author ID
55735983400 55735983400
CreatorName
Hayashi, Takashi
Subject
Artificial metalloenzyme
Dihydroisoquinoline
Excited state
Imine reduction
Peptide
Photoredox reaction
Description
Kano R., Oohora K., Hayashi T. Photo-induced imine reduction by a photoredox biocatalyst consisting of a pentapeptide and a Ru bipyridine terpyridine complex. Journal of Inorganic Biochemistry 259, 112657 (2024); https://doi.org/10.1016/j.jinorgbio.2024.112657.
Abstract
Imine reduction is a useful reaction in the preparation of amine derivatives. Various catalysts have been reported to promote this reaction and photoredox catalysts are promising candidates for sustainable amine synthesis. Improvement of this reaction using biomolecule-based reaction scaffolds is expected to increase the utility of the reaction. In this context, we have recently investigated photoredox Ru complexes with pentapeptide scaffolds via coordination bonds as catalysts for photoreduction of dihydroisoquinoline derivatives. First, Ru bipyridine terpyridine complexes coordinated with five different pentapeptides (XVHVV: X = V, F, W, Y, C) were prepared and characterized by mass spectrometry. Catalytic activities of the Ru complexes with XVHVV were evaluated for photoreduction of dihydroisoquinoline derivatives in the presence of ascorbate and thiol compounds as sacrificial reagents and hydrogen sources. Interestingly, the turnover number of the Ru complex with VVHVV is 531, which is two-fold higher than that of a simple Ru complex with an imidazole ligand. The detailed emission lifetime measurements indicate that the enhanced catalytic activity provided by the peptide scaffold is caused by an efficient reaction with the thiol derivative to accelerate reductive quenching of Ru complex. The quenching behavior suggests formation of an active species such as a Ru(I) complex. These findings reveal that the simple pentapeptide serves as an effective scaffold to enhance the photocatalytic activity of a photoactive Ru complex.
Publisher
Elsevier Inc.
Source Title
Journal of Inorganic Biochemistry
Volume (Issue)
259
Page
112657
Date of Issued
2024-10-01
Language
English
Handle URL
https://hdl.handle.net/11094/98160
PISSN
01620134
eISSN
18733344
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1016/j.jinorgbio.2024.112657
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article