5,5-Dimethylproline dipeptides: Anacid-stable class of pseudoproline

Bianca Jane Van Lierop, William Roy Jackson, Andrea Jane Robinson

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Abstract

Commercially available Fmoc-protected L-amino acids were employed and coupled to L-allylglycine. Cross metathesis with 2-methyl-2-butene using second generation Grubbs catalyst gave L-prenylglycine-containing dipeptides. Treatment with trifluoromethanesulfonic acid resulted in cyclisation and subsequent formation of acid-stable 5,5-dimethyl-L-proline dipeptides for direct insertion into linear peptide sequences.
Original languageEnglish
Pages (from-to)5357 - 5366
Number of pages10
JournalTetrahedron
Volume66
Issue number29
DOIs
Publication statusPublished - 2010

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