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Sequence-specific recognition of right-handed double-helical DNA by (2S,3S)- and (2R,3R)-dihydroxybis(netropsin)succinamide

Griffin, John H. and Dervan, Peter B. (1986) Sequence-specific recognition of right-handed double-helical DNA by (2S,3S)- and (2R,3R)-dihydroxybis(netropsin)succinamide. Journal of the American Chemical Society, 108 (16). pp. 5008-5009. ISSN 0002-7863. doi:10.1021/ja00276a052.

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We report a class of chiral sequence-specific DNA binding molecules based on two netropsin analogues and the enantiomers of dl-tartaric acid: (2R,3R)- and (2S,3S)-dihydroxybis(netropsin)succinamide-EDTA [(R,R)- and (S,S)-1, respectively] (Figures 1 and 2). The enantiomeric threo-(R,R)1 and -(SS)-1 should afford diastereomeric complexes at common binding sites on double-helical DNA (Figure 1). Attachment of EDTA to one terminus of the crescent-shaped hexamides allows use of the affinity cleaving method to determine the differences between (R,R)-1•Fe^(II) and (S,S)-1•Fe^(II) with regard to relative binding affinities, sequence specificities, and orientations by analysis of the DNA-cleavage patterns on a 32P end-labeled DNA restriction fragment using high-resolution gel electrophoresis. For comparison to the enantiomers of 1, bis(netropsin)succinamide-EDTA (2) was synthesized (Figure 2).

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Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 1986 American Chemical Society. Received March 10, 1986. We are grateful to the National Institutes of Health for research support (GM-27681) and to the National Science Foundation for a predoctoral fellowship to J.H.G.
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NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:16
Record Number:CaltechAUTHORS:20160511-145736773
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Official Citation:Specific sequence-specific recognition of right-handed double-helical DNA by (2S,3S)- and (2R,3R)-dihydroxybis(netropsin)succinamide John H. Griffin and Peter B. Dervan Journal of the American Chemical Society 1986 108 (16), 5008-5009 DOI: 10.1021/ja00276a052
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:67014
Deposited By: Victoria Brennan
Deposited On:19 May 2016 20:17
Last Modified:11 Nov 2021 00:25

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