Synthesis and spectroscopic characterization of binaphthol aminosugars for stimulation of DNA strand slippage synthesis

Liangliang Liu; Long Yi; Xing Yang; Zhihong Yu; Xin Wen; Zhen Xi

doi:10.1016/j.tet.2008.04.047

Synthesis and spectroscopic characterization of binaphthol aminosugars for stimulation of DNA strand slippage synthesis

Liangliang Liu, Long Yi, Xing Yang, Zhihong Yu, Xin Wen, Zhen Xi

School of Medicine

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Expansion of DNA repeat sequences is associated with many human genetic diseases. Bulged DNA structures have been implicated as intermediates in DNA slippage within the DNA repeat regions. Two new binaphthol aminosugars were first synthesized as DNA bulge binders to study the triplet repeat expansion due to the wedge-shaped structure of 1,1′-bi-2-naphthol. Both compounds were structurally characterized by 1- and 2-D NMR. They showed remarkable fluorescence enhancement when binding with bulge DNA and they exhibited stimulation for ATT·AAT trinucleotide repeat DNA sequence slippage synthesis.

Original language	English (US)
Pages (from-to)	5885-5890
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2008.04.047
State	Published - Jun 16 2008

Keywords

Binaphthol
DNA
Slippage synthesis
Trinucleotide repeat
Wedge-shaped structure

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.04.047

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title = "Synthesis and spectroscopic characterization of binaphthol aminosugars for stimulation of DNA strand slippage synthesis",

abstract = "Expansion of DNA repeat sequences is associated with many human genetic diseases. Bulged DNA structures have been implicated as intermediates in DNA slippage within the DNA repeat regions. Two new binaphthol aminosugars were first synthesized as DNA bulge binders to study the triplet repeat expansion due to the wedge-shaped structure of 1,1′-bi-2-naphthol. Both compounds were structurally characterized by 1- and 2-D NMR. They showed remarkable fluorescence enhancement when binding with bulge DNA and they exhibited stimulation for ATT·AAT trinucleotide repeat DNA sequence slippage synthesis.",

keywords = "Binaphthol, DNA, Slippage synthesis, Trinucleotide repeat, Wedge-shaped structure",

author = "Liangliang Liu and Long Yi and Xing Yang and Zhihong Yu and Xin Wen and Zhen Xi",

note = "Funding Information: We thank NSFC, NSF of Tianjin (013616311), MOST (2003CB114403) and MOE of China for financial support. ",

year = "2008",

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doi = "10.1016/j.tet.2008.04.047",

language = "English (US)",

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T1 - Synthesis and spectroscopic characterization of binaphthol aminosugars for stimulation of DNA strand slippage synthesis

AU - Liu, Liangliang

AU - Yi, Long

AU - Yang, Xing

AU - Yu, Zhihong

AU - Wen, Xin

AU - Xi, Zhen

N1 - Funding Information: We thank NSFC, NSF of Tianjin (013616311), MOST (2003CB114403) and MOE of China for financial support.

PY - 2008/6/16

Y1 - 2008/6/16

N2 - Expansion of DNA repeat sequences is associated with many human genetic diseases. Bulged DNA structures have been implicated as intermediates in DNA slippage within the DNA repeat regions. Two new binaphthol aminosugars were first synthesized as DNA bulge binders to study the triplet repeat expansion due to the wedge-shaped structure of 1,1′-bi-2-naphthol. Both compounds were structurally characterized by 1- and 2-D NMR. They showed remarkable fluorescence enhancement when binding with bulge DNA and they exhibited stimulation for ATT·AAT trinucleotide repeat DNA sequence slippage synthesis.

AB - Expansion of DNA repeat sequences is associated with many human genetic diseases. Bulged DNA structures have been implicated as intermediates in DNA slippage within the DNA repeat regions. Two new binaphthol aminosugars were first synthesized as DNA bulge binders to study the triplet repeat expansion due to the wedge-shaped structure of 1,1′-bi-2-naphthol. Both compounds were structurally characterized by 1- and 2-D NMR. They showed remarkable fluorescence enhancement when binding with bulge DNA and they exhibited stimulation for ATT·AAT trinucleotide repeat DNA sequence slippage synthesis.

KW - Binaphthol

KW - DNA

KW - Slippage synthesis

KW - Trinucleotide repeat

KW - Wedge-shaped structure

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Synthesis and spectroscopic characterization of binaphthol aminosugars for stimulation of DNA strand slippage synthesis

Abstract

Keywords

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