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Title: Development of DNA Metalloenzymes Using a Rational Design Approach and Application in the Asymmetric Diels-Alder Reaction
Authors: Park, Soyoung  kyouindb  KAKEN_id
Okamura, Izumi
Sakashita, Sohei
Yum, Ji Hye
Acharya, Chiranjit
Gao, Li
Sugiyama, Hiroshi
Author's alias: 朴, 昭映
岡村, 和泉
坂下, 宗平
杉山, 弘
Keywords: asymmetric catalysis
Cu(II) ion
Diels-Alder reaction
DNA
enantiomeric preference
ligand freedom
metalloenzyme
Issue Date: 7-Aug-2015
Publisher: American Chemical Society
Journal title: ACS Catalysis
Volume: 5
Issue: 8
Start page: 4708
End page: 4712
Abstract: We report here DNA metalloenzymes that catalyzed the asymmetric Diels-Alder reactions with high conversion, excellent endo/exo selectivities, and enantioselectivities up to -97% ee. Their catalytic-pocket architectures were organized using a rational design strategy based on the Cu(II) ion, the composition of nucleobases, and the incorporation of flexible linkers. Without using the mirror image of B-DNA, DNA metalloenzymes afforded the opposite enantiomer of the Diels-Alder product compared with those obtained using a supramolecular Cu(II)-dmbpy/st-DNA catalyst system. Furthermore, we devised DNA metalloenzymes without the incorporation of an artificial binding ligand and successfully performed Diels-Alder carbon-carbon bond-forming reactions. This study provides a new perspective on the catalytic repertoire of nucleic acids in the realm of protein-dominated metalloenzymes.
Rights: © 2015 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see 10.1021/acscatal.5b01046. The full-text file will be made open to the public on 07 August 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/230917
DOI(Published Version): 10.1021/acscatal.5b01046
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