TY - JOUR
T1 - Quaternary amine-induced peptide degradation via cyclization
AU - Than, Chistopher Trong Linh
AU - Ferguson, Glen Allen
AU - Raghavachari, Krishnan
PY - 2010/1/14
Y1 - 2010/1/14
N2 - 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.
AB - 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.
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U2 - 10.1021/jp906646n
DO - 10.1021/jp906646n
M3 - Article
C2 - 19968311
AN - SCOPUS:75249099680
SN - 1089-5639
VL - 114
SP - 481
EP - 485
JO - Journal of Physical Chemistry A
JF - Journal of Physical Chemistry A
IS - 1
ER -