Facile synthesis of oligopeptide distamycin analogs devoid of hydrogen bond donors or acceptors at the N-terminus: sequence-specific duplex DNA binding as a function of peptide chain length

Bhattacharya, Santanu and Thomas, Mini (2000) Facile synthesis of oligopeptide distamycin analogs devoid of hydrogen bond donors or acceptors at the N-terminus: sequence-specific duplex DNA binding as a function of peptide chain length. In: Tetrahedron Letters, 41 (29). pp. 5571-5575.

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Abstract

The first examples of distamycin analogs, which lack hydrogen bond interactor groups at the N-terminus, have been synthesized. The bispyrrole peptide did not exhibit any detectable binding with double-stranded (ds) DNA. However, all other homologues did bind to ds-DNA strongly, with the binding affinities increasing as a function of the number of repeating pyrrole carboxamide units, implying that a hydrogen bond donor or acceptor atom per se at the N-terminus is not essential for their DNA binding. Studies with poly d(GC) showed that the N-terminal formamide is not a prerequisite for GC binding, contrary to earlier postulations.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier Science Ltd.
Additional Information:	Copyright of this article belongs to Elsevier Science Ltd
Keywords:	Molecular Genetics;Biochemistry and Molecular Biophysics;Methods and Techniques;Pharmacology
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	17 Oct 2007
Last Modified:	19 Sep 2010 04:40
URI:	http://eprints.iisc.ac.in/id/eprint/12116

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