Synthesis of 3,3'-di-O-methyl ardimerin and exploration of its DNA binding properties.
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.
Department of Chemistry and Biochemistry, California State University , Northridge 18111 Nordhoff Street, Northridge, California 91330, United States.
Miran
M
Mavlan
Kevin
K
Ng
Harmanpreet
H
Panesar
Akop
A
Yepremyan
Thomas G
TG
Minehan
D000840:Anisoles / Q000737:chemistry; D004247:DNA / Q000378:metabolism*; D005453:Fluorescence; D006031:Glycosylation; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
C000590014:3,3'-di-O-methylardimerin; D000840:Anisoles; D007783:Lactones; D004247:DNA; C091694:1,2,3-trimethoxybenzene