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

[Image: see text] 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 glycosyl...

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Autores principales: Mavlan, Miran, Ng, Kevin, Panesar, Harmanpreet, Yepremyan, Akop, Minehan, Thomas G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4067242/
https://www.ncbi.nlm.nih.gov/pubmed/24712737
http://dx.doi.org/10.1021/ol500725e
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author Mavlan, Miran
Ng, Kevin
Panesar, Harmanpreet
Yepremyan, Akop
Minehan, Thomas G.
author_facet Mavlan, Miran
Ng, Kevin
Panesar, Harmanpreet
Yepremyan, Akop
Minehan, Thomas G.
author_sort Mavlan, Miran
collection PubMed
description [Image: see text] 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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spelling pubmed-40672422015-04-09 Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties Mavlan, Miran Ng, Kevin Panesar, Harmanpreet Yepremyan, Akop Minehan, Thomas G. Org Lett [Image: see text] 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. American Chemical Society 2014-04-09 2014-04-18 /pmc/articles/PMC4067242/ /pubmed/24712737 http://dx.doi.org/10.1021/ol500725e Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Mavlan, Miran
Ng, Kevin
Panesar, Harmanpreet
Yepremyan, Akop
Minehan, Thomas G.
Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties
title Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties
title_full Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties
title_fullStr Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties
title_full_unstemmed Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties
title_short Synthesis of 3,3′-Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties
title_sort synthesis of 3,3′-di-o-methyl ardimerin and exploration of its dna binding properties
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4067242/
https://www.ncbi.nlm.nih.gov/pubmed/24712737
http://dx.doi.org/10.1021/ol500725e
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