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 › peer-review

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

Access to Document

10.1021/ol048152c

Fingerprint Dive into the research topics of 'Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder'. Together they form a unique fingerprint.

Cite this

@article{308e738932904f159b1bb9194bae096c,

title = "Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder",

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.",

author = "Gaikwad, {Nilesh W.} and Hwang, {Geum Sook} and Goldberg, {Irving H.}",

year = "2004",

month = dec,

day = "23",

doi = "10.1021/ol048152c",

language = "English (US)",

volume = "6",

pages = "4833--4836",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

T1 - Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder

AU - Gaikwad, Nilesh W.

AU - Hwang, Geum Sook

AU - Goldberg, Irving H.

PY - 2004/12/23

Y1 - 2004/12/23

N2 - (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.

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.

UR - http://www.scopus.com/inward/record.url?scp=12344310133&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=12344310133&partnerID=8YFLogxK

U2 - 10.1021/ol048152c

DO - 10.1021/ol048152c

M3 - Article

C2 - 15606078

AN - SCOPUS:12344310133

VL - 6

SP - 4833

EP - 4836

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 26

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this