Synthesis of Pyrrolidinyl PNA and Its Site-Specific Labeling at Internal Positions by Click Chemistry

Boonsong Ditmangklo; Penthip Muangkaew; Kotchakorn Supabowornsathit; Tirayut Vilaivan

doi:10.1007/978-1-0716-0243-0_3

Synthesis of Pyrrolidinyl PNA and Its Site-Specific Labeling at Internal Positions by Click Chemistry

Methods Mol Biol. 2020:2105:35-60. doi: 10.1007/978-1-0716-0243-0_3.

Authors

Boonsong Ditmangklo¹, Penthip Muangkaew¹, Kotchakorn Supabowornsathit¹, Tirayut Vilaivan²

Affiliations

¹ Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
² Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand. [email protected].

PMID: 32088863
DOI: 10.1007/978-1-0716-0243-0_3

Abstract

Pyrrolidinyl PNA with an α-/β-dipeptide backbone consisting of alternating nucleobase-modified D-proline and (1S,2S)-2-aminocyclopentanecarboxylic acid (also known as acpcPNA) is a class of conformationally constrained PNA that shows exceptional DNA hybridization properties including very high specificity and the inability to form self-pairing hybrids. In this chapter, details of the syntheses of acpcPNA as well as its monomers and a protocol for site-specific labeling with a fluorescent dye via click chemistry are reported.

Keywords: AcpcPNA; Click chemistry; Labeling; PNA synthesis; Pyrrolidinyl PNA.

MeSH terms

Alkylation
Chemistry Techniques, Synthetic
Click Chemistry* / methods
Molecular Structure
Peptide Nucleic Acids / chemical synthesis*
Peptide Nucleic Acids / chemistry
Peptide Nucleic Acids / isolation & purification
Staining and Labeling*

Substances

Peptide Nucleic Acids