Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection

Digvijay Gahtory; Merita Murtola; Maarten M J Smulders; Tom Wennekes; Han Zuilhof; Roger Strömberg; Bauke Albada

doi:10.1039/c7ob01592e

Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection

Digvijay Gahtory, Merita Murtola, Maarten M J Smulders, Tom Wennekes, Han Zuilhof, Roger Strömberg, Bauke Albada

Laboratory of Organic Chemistry, Wageningen University and Research, Stippeneng 4, 6708 WE Wageningen, The Netherlands. [email protected] [email protected].

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

Abstract

In this report, we show how a convenient on-resin copper-click functionalization of azido-functionalized peptide nucleic acids (PNAs) allows various PNA-based detection strategies. Firstly, a thiazole orange (TO) clicked PNA probe facilitates a binary readout when combined with F/Q labeled DNA, giving increased sensitivity for antisense detection. Secondly, our TO-PNA conjugate also allows single nucleotide polymorphism detection. Since antisense detection is also possible in the absence of the TO label, our sensing platform based on azido-d-ornithine containing PNA even allows for additional and more advanced functionalization and sensing strategies.

Original language	English
Pages (from-to)	6710-6714
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	32
DOIs	https://doi.org/10.1039/c7ob01592e
Publication status	Published - 16 Aug 2017

Keywords

Azides
Benzothiazoles
Copper
DNA, Antisense
Molecular Probes
Peptide Nucleic Acids
Polymorphism, Single Nucleotide
Quinolines

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10.1039/c7ob01592e

gahtoryFinal published version, 1.74 MBLicence: Taverne

Cite this

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title = "Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection",

abstract = "In this report, we show how a convenient on-resin copper-click functionalization of azido-functionalized peptide nucleic acids (PNAs) allows various PNA-based detection strategies. Firstly, a thiazole orange (TO) clicked PNA probe facilitates a binary readout when combined with F/Q labeled DNA, giving increased sensitivity for antisense detection. Secondly, our TO-PNA conjugate also allows single nucleotide polymorphism detection. Since antisense detection is also possible in the absence of the TO label, our sensing platform based on azido-d-ornithine containing PNA even allows for additional and more advanced functionalization and sensing strategies.",

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T1 - Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection

AU - Gahtory, Digvijay

AU - Murtola, Merita

AU - Smulders, Maarten M J

AU - Wennekes, Tom

AU - Zuilhof, Han

AU - Strömberg, Roger

AU - Albada, Bauke

PY - 2017/8/16

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AB - In this report, we show how a convenient on-resin copper-click functionalization of azido-functionalized peptide nucleic acids (PNAs) allows various PNA-based detection strategies. Firstly, a thiazole orange (TO) clicked PNA probe facilitates a binary readout when combined with F/Q labeled DNA, giving increased sensitivity for antisense detection. Secondly, our TO-PNA conjugate also allows single nucleotide polymorphism detection. Since antisense detection is also possible in the absence of the TO label, our sensing platform based on azido-d-ornithine containing PNA even allows for additional and more advanced functionalization and sensing strategies.

KW - Azides

KW - Benzothiazoles

KW - Copper

KW - DNA, Antisense

KW - Molecular Probes

KW - Peptide Nucleic Acids

KW - Polymorphism, Single Nucleotide

KW - Quinolines

U2 - 10.1039/c7ob01592e

DO - 10.1039/c7ob01592e

M3 - Article

C2 - 28766647

SN - 1477-0520

VL - 15

SP - 6710

EP - 6714

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 32

ER -

Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection

Abstract

Keywords

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