Conformational analysis of a covalently cross-linked Watson-Crick base pair model

Erik A. Jensen; Benjamin D. Allen; Yoshito Kishi; Daniel J. O'Leary

doi:10.1016/j.bmcl.2008.07.113

Conformational analysis of a covalently cross-linked Watson-Crick base pair model

Erik A. Jensen, Benjamin D. Allen, Yoshito Kishi, Daniel J. O'Leary

Biochemistry & Molecular Biology

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

Abstract

Low-temperature NMR experiments and molecular modeling have been used to characterize the conformational behavior of a covalently cross-linked DNA base pair model. The data suggest that Watson-Crick or reverse Watson-Crick hydrogen bonding geometries have similar energies and can interconvert at low temperatures. This low-temperature process involves rotation about the crosslink CH₂{single bond}C(5′) (ψ) carbon-carbon bond, which is energetically preferred over the alternate CH₂{single bond}N(3) (φ) carbon-nitrogen bond rotation.

Original language	English (US)
Pages (from-to)	5884-5887
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2008.07.113
State	Published - Nov 15 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2008.07.113

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title = "Conformational analysis of a covalently cross-linked Watson-Crick base pair model",

abstract = "Low-temperature NMR experiments and molecular modeling have been used to characterize the conformational behavior of a covalently cross-linked DNA base pair model. The data suggest that Watson-Crick or reverse Watson-Crick hydrogen bonding geometries have similar energies and can interconvert at low temperatures. This low-temperature process involves rotation about the crosslink CH2{single bond}C(5′) (ψ) carbon-carbon bond, which is energetically preferred over the alternate CH2{single bond}N(3) (φ) carbon-nitrogen bond rotation.",

author = "Jensen, {Erik A.} and Allen, {Benjamin D.} and Yoshito Kishi and O'Leary, {Daniel J.}",

note = "Funding Information: This letter is dedicated to Professor Benjamin F. Cravatt on the occasion of his Tetrahedron Young Investigator Award in Bioorganic and Medicinal Chemistry. Financial support from the National Science Foundation, the Camille and Henry Dreyfus Foundation, and the National Institutes of Health (NS 12108) is gratefully acknowledged. B.D.A. is a Beckman Scholar. We thank Professors Jay Siegel (University of Zurich), Frank Anet (University of California, Los Angeles), and Wayne Steinmetz (Pomona College) for helpful discussions. ",

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doi = "10.1016/j.bmcl.2008.07.113",

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AU - Kishi, Yoshito

AU - O'Leary, Daniel J.

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Conformational analysis of a covalently cross-linked Watson-Crick base pair model

Abstract

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