Letters in Peptide Science

, Volume 9, Issue 4, pp 211–219

A rapid coupling protocol for the synthesis of peptide nucleic acids

Article

DOI: 10.1007/BF02538386

Cite this article as:
Vearing, C.J. & Fecondo, J.V. Lett Pept Sci (2002) 9: 211. doi:10.1007/BF02538386
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Summary

With the current interest in anti-sense and anti-gene technologies, an efficient, fast and less toxic synthesis protocol would be advantageous for the oligomerisation of Peptide Nucleic Acids (PNA). Most of the methods currently in use for thet-Boc synthesis of PNA's use TFA/m-cresol, pyridine, piperidine and capping reagents. In this work, a rapid synthesis protocol has been adapted from an earlier published peptide synthesis method allowing a reduction in cycle time from around 30 min down to 16 min. By utilising quantitative deprotection with 100% TFA, a coupling time of 10 min and a four-fold excess of monomer, this synthesis protocol has been used to synthesise a number of PNA's incorporating all four nucleotides of varying sequence, up to 17 residues in length.

Key words

anti-sense/anti-gene oligonucleotide peptide nucleic acid PNA SPPS 

Abbreviations

DCM

dichloromethane

DECA

N, N-diethylcyclohexylamine

DIEA

N, N-diisopropylethylamine

DMF

N, N-dimethylformamide

HBTU

2-benzotriazole-N, N, N′, N′-tetramethyl-uronium-hexafluorophosphate

mBHA

4-methylbenzhydrylamine

TFA

trifluoroacetic acid

TFMSA

trifluoromethanesulfonic acid

Copyright information

© Kluwer Academic Publishers 2003

Authors and Affiliations

  1. 1.School of Engineering and ScienceSwinburne University of TechnologyHawthornAustralia
  2. 2.Department of Biotechnology and Environmental BiologyRMIT UniversityBundooraAustralia

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