Synthesis of 3,3'-di-O-methyl ardimerin and exploration of its DNA binding properties

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

doi:10.1021/ol500725e

Synthesis of 3,3'-di-O-methyl ardimerin and exploration of its DNA binding properties

Org Lett. 2014 Apr 18;16(8):2212-5. doi: 10.1021/ol500725e. Epub 2014 Apr 9.

Authors

Miran Mavlan¹, Kevin Ng, Harmanpreet Panesar, Akop Yepremyan, Thomas G Minehan

Affiliation

¹ Department of Chemistry and Biochemistry, California State University , Northridge 18111 Nordhoff Street, Northridge, California 91330, United States.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Anisoles / chemistry
DNA / metabolism*
Fluorescence
Glycosylation
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure

Substances

3,3'-di-O-methylardimerin
Anisoles
Lactones
DNA
1,2,3-trimethoxybenzene

Abstract

Publication types

MeSH terms

Substances

Grants and funding