Synthesis and application of LKγT peptide nucleic acids

Nathaniel Shank, Kara M. George Rosenker, Ethan A. Englund, Andrew V. Dix, Elizabeth E. Rastede, Daniel H. Appella

Research output: Contribution to book or proceedingChapterpeer-review

Abstract

Displaying ligands in a succinct and predictable manner is essential for elucidating multivalent molecular-level binding events. Organizing ligands with high precision and accuracy provides a distinct advantage over other ligand-display systems, such as polymers, because the number and position of the ligand(s) can be accurately and fully characterized. Here we describe the synthesis of peptide nucleic acids (PNAs), which are oligonucleotide mimics with a pseudopeptide backbone that can hybridize to oligonucleotides through Watson-Crick base pair to form highly predictable and organized scaffold for organizing a ligand. The ligand(s) are covalently attached to the PNA through a squarate coupling reaction that occurs between a free amine on the ligand and a free amine appended to the pseudopeptide backbone of the PNA. In this chapter we describe the synthesis of a LKγT monomer, which ultimately yields the free amine off the backbone of the PNA, incorporation of the monomer in a PNA oligomer, and the sequential squarate coupling to conjugate the ligand.

Original languageEnglish
Title of host publicationMethods in Molecular Biology
PublisherHumana Press Inc.
Pages131-145
Number of pages15
DOIs
StatePublished - 2019

Publication series

NameMethods in Molecular Biology
Volume1973
ISSN (Print)1064-3745
ISSN (Electronic)1940-6029

Scopus Subject Areas

  • Molecular Biology
  • Genetics

Keywords

  • Ligand organization
  • Molecular scaffold
  • Multivalent interactions
  • Nonnatural nucleic acid
  • Peptide nucleic acid

Fingerprint

Dive into the research topics of 'Synthesis and application of LKγT peptide nucleic acids'. Together they form a unique fingerprint.

Cite this