Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties | Zendy

Miran Mavlan | Zendy; Kevin Ng | Zendy; Harmanpreet Panesar | Zendy; Akop Yepremyan | Zendy; Thomas G. Minehan | Zendy

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Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties

Author(s) -

Miran Mavlan,

Kevin Ng,

Harmanpreet Panesar,

Akop Yepremyan,

Thomas G. Minehan

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol500725e

Subject(s) - chemistry , dna , stereochemistry , combinatorial chemistry , biochemistry

The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 μM, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.

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