Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

Robert S. Coleman; Mark A. Berg; Catherine J. Murphy

doi:10.1016/j.tet.2006.12.096

Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

Robert S. Coleman, Mark A. Berg, Catherine J. Murphy

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

Abstract

The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods.

Original language	English (US)
Pages (from-to)	3450-3456
Number of pages	7
Journal	Tetrahedron
Volume	63
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2006.12.096
State	Published - Apr 23 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.12.096

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abstract = "The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods.",

author = "Coleman, {Robert S.} and Berg, {Mark A.} and Murphy, {Catherine J.}",

note = "Funding Information: This work was funded by a grant from the National Institutes of Health (R01GM61292).",

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AU - Coleman, Robert S.

AU - Berg, Mark A.

AU - Murphy, Catherine J.

N1 - Funding Information: This work was funded by a grant from the National Institutes of Health (R01GM61292).

PY - 2007/4/23

Y1 - 2007/4/23

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AB - The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods.

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

Abstract

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