Quaternary amine-induced peptide degradation via cyclization

Chistopher Trong Linh Than, Glen Allen Ferguson, Krishnan Raghavachari

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Abstract

In this study, we investigated intramolecular cyclizations in peptides containing quaternary amines. Two types of cyclization reactions are studied: (a) those involving a trimethylammonium butyric acid (TMAB) charge tag and (b) those involving trimethylated lysine. Both types of reactions result in the release of trimethy lamine via an Sn2 mechanism involving a lone pair of electrons on the oxygen or nitrogen. In the case of the TMAB charge tag cyclization, the oxygen attack mechanism leading to a five-membered ring is the preferred pathway. In the trimethylated lysine cyclizations, the preferred pathway involves the nitrogen nucleophile resulting in the formation of a six-membered ring. The similarities and differences between the two reactions are analyzed.

Original languageEnglish (US)
Pages (from-to)481-485
Number of pages5
JournalJournal of Physical Chemistry A
Volume114
Issue number1
DOIs
Publication statusPublished - Jan 14 2010

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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