Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder

Nilesh W. Gaikwad; Geum Sook Hwang; Irving H. Goldberg

doi:10.1021/ol048152c

Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder

Nilesh W. Gaikwad, Geum Sook Hwang, Irving H. Goldberg

Research output: Contribution to journal › Article

9 Scopus citations

Abstract

(Chemical Equation Presented) Synthesis of chiral spirocyclic helical compounds which mimic the molecular architecture of the potent DNA bulge binder obtained from the antitumor agent NCS-chrom has been accomplished. Structural analysis of the compounds by CD and NMR is presented. NMR titration study indicates binding of P,α-helimer (1d) at a two-base bulge site in a DNA oligomer, providing insight to the design of agents as specific probes of a bulged structure in nucleic acids.

Original language	English (US)
Pages (from-to)	4833-4836
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	26
DOIs	https://doi.org/10.1021/ol048152c
State	Published - Dec 23 2004
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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10.1021/ol048152c

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Gaikwad, N. W., Hwang, G. S., & Goldberg, I. H. (2004). Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder. Organic Letters, 6(26), 4833-4836. https://doi.org/10.1021/ol048152c

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abstract = "(Chemical Equation Presented) Synthesis of chiral spirocyclic helical compounds which mimic the molecular architecture of the potent DNA bulge binder obtained from the antitumor agent NCS-chrom has been accomplished. Structural analysis of the compounds by CD and NMR is presented. NMR titration study indicates binding of P,α-helimer (1d) at a two-base bulge site in a DNA oligomer, providing insight to the design of agents as specific probes of a bulged structure in nucleic acids.",

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AU - Hwang, Geum Sook

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AB - (Chemical Equation Presented) Synthesis of chiral spirocyclic helical compounds which mimic the molecular architecture of the potent DNA bulge binder obtained from the antitumor agent NCS-chrom has been accomplished. Structural analysis of the compounds by CD and NMR is presented. NMR titration study indicates binding of P,α-helimer (1d) at a two-base bulge site in a DNA oligomer, providing insight to the design of agents as specific probes of a bulged structure in nucleic acids.

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