合成 3,3'-二-O-甲基 Ardimerin 并探索其与 DNA 的结合特性。

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

机构信息

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

出版信息

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

DOI:10.1021/ol500725e

PMID:24712737

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4067242/

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.

摘要

双 C-芳基糖苷天然产物 Ardimerin（1）的 3,3'-二-O-甲基衍生物（15）已通过 2,3,4,6-四苄基葡萄糖（2）和 1,2,3-三甲氧基苯（3）从 11 步合成。合成中的关键步骤包括路易斯酸介导的 Friedel-Crafts 型糖苷化和在 Yonemitsu 条件下的 Yamaguchi 内酯化。3,3'-二-O-甲基 Ardimerin 在浓度大于 1 μM 的水溶液中聚集，并且 UV 和荧光结合研究表明 15 与双链 DNA 的亲和力低。