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Generation of DNA interstrand cross-links by post-synthetic reductive amination


Angelov, Todor; Guainazzi, Angelo; Schärer, Orlando D (2009). Generation of DNA interstrand cross-links by post-synthetic reductive amination. Organic Letters, 11(3):661-664.

Abstract

DNA interstrand cross-links (ICLs) are the clinically most relevant adducts formed by many antitumor agents. To facilitate the study of biological responses triggered by ICLs, we developed a new approach toward the synthesis of mimics of nitrogen mustard ICLs. 7-Deazaguanine residues bearing acetaldehyde groups were incorporated into complementary strands of DNA and cross-link formation induced by double reductive amination. Our strategy enables the synthesis of major groove cross-links in high yields and purity.

Abstract

DNA interstrand cross-links (ICLs) are the clinically most relevant adducts formed by many antitumor agents. To facilitate the study of biological responses triggered by ICLs, we developed a new approach toward the synthesis of mimics of nitrogen mustard ICLs. 7-Deazaguanine residues bearing acetaldehyde groups were incorporated into complementary strands of DNA and cross-link formation induced by double reductive amination. Our strategy enables the synthesis of major groove cross-links in high yields and purity.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > Institute of Molecular Cancer Research
07 Faculty of Science > Institute of Molecular Cancer Research
Dewey Decimal Classification:570 Life sciences; biology
Language:English
Date:2009
Deposited On:04 Jul 2012 16:23
Last Modified:08 Aug 2017 07:04
Publisher:American Chemical Society
ISSN:1523-7052
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.1021/ol802719a
PubMed ID:19132933

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