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Synfacts 2016; 12(1): 0095
DOI: 10.1055/s-0035-1561087
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper/DNA G-Quadruplex-Catalyzed Diels–Alder Reaction

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Li Y, Cheng M, Hao J, Wang C, Jia G, * Li C. * University of Chinese Academy of Sciences, Beijing and Dalian Institute of Chemical Physics, P. R. of China
Terpyridine-Cu(II) Targeting Human Telomeric DNA to Produce Highly Stereospecific G-quadruplex DNA Metalloenzyme.

Chem. Sci. 2015;
6: 5578-5585
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Publication History

Publication Date:
16 December 2015 (online)

 
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Key words

DNA - copper catalysis - metalloenzymes - Diels–Alder reaction - azachalcones

Significance

A terpyridine–copper(II) complex supported on human telomeric G-quadruplex DNA (HT-21-A) was prepared by treatment of HT-21 with the copper–terpyridine complex A in the presence of NH4Cl. HT-21-A catalyzed the ­enantioselective Diels–Alder reaction of azachalcones with cyclopentadiene to give the corresponding products in >99% conversion, ≤99:1 endo/exo selectivity, and ≤99% ee.


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Comment

The formation of HT-21-A was confirmed by CD-spectroscopic analysis, UV melting, and ITC experiments. In the reaction of 3-phenyl-1-(pyridin-2-yl)prop-2-en-1-one with cyclopentadiene, HT-21-A promoted the enantioselective Diels–Alder reaction with about a 73-fold rate acceleration compared with the copper complex A alone.


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