A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA

Michael C. Myers; Mark A. Witschi; Nataliya V. Larionova; John M. Franck; Russell D. Haynes; Toshiaki Hara; Andrzej Grajkowski; Daniel H. Appella

doi:10.1021/ol0348811

A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA

Michael C. Myers, Mark A. Witschi, Nataliya V. Larionova, John M. Franck, Russell D. Haynes, Toshiaki Hara, Andrzej Grajkowski, Daniel H. Appella

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

54 Scopus citations

Abstract

(Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.

Original language	English (US)
Pages (from-to)	2695-2698
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	15
DOIs	https://doi.org/10.1021/ol0348811
State	Published - Jul 24 2003
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0348811

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title = "A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA",

abstract = "(Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.",

author = "Myers, {Michael C.} and Witschi, {Mark A.} and Larionova, {Nataliya V.} and Franck, {John M.} and Haynes, {Russell D.} and Toshiaki Hara and Andrzej Grajkowski and Appella, {Daniel H.}",

year = "2003",

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doi = "10.1021/ol0348811",

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T1 - A cyclopentane conformational restraint for a peptide nucleic acid

T2 - Design, asymmetric synthesis, and improved binding affinity to DNA and RNA

AU - Myers, Michael C.

AU - Witschi, Mark A.

AU - Larionova, Nataliya V.

AU - Franck, John M.

AU - Haynes, Russell D.

AU - Hara, Toshiaki

AU - Grajkowski, Andrzej

AU - Appella, Daniel H.

PY - 2003/7/24

Y1 - 2003/7/24

N2 - (Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.

AB - (Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.

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JO - Organic Letters

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A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA

Abstract

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