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Expanding the repertoire of natural product-inspired ring pairs for molecular recognition of DNA.

Authors
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Volume
13
Issue
20
Pages
5612–5615
Identifiers
DOI: 10.1021/ol202285y
Source
UCSC Cancer biomedical-ucsc
License
Unknown

Abstract

A furan amino acid, inspired by the recently discovered proximicin natural products, was incorporated into the scaffold of a DNA-binding hairpin polyamide. While unpaired oligomers of 2,4-disubstituted furan amino acids show poor DNA-binding activity, furan (Fn) carboxamides paired with N-methylpyrrole (Py) and N-methylimidazole (Im) rings demonstrate excellent stabilization of duplex DNA as well as discrimination of noncognate sequences, consistent with function as a Py mimic according to the Py/Im polyamide pairing rules.

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