5,5-Dimethylproline dipeptides: an acid-stable class of pseudoproline

作者：van Lierop Bianca J; Jackson W Roy; Robinson Andrea J^*

来源：Tetrahedron, 2010, 66(29): 5357-5366.

DOI：10.1016/j.tet.2010.05.068

• Pseudoproline residues
• 5,5-Dimethyl-L-proline
• Cis-trans isomerisation
• Cisoidal amide bond
• Cross metathesis (CM)
• Acid-catalysed cyclisation

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.

• 出版日期2010-7-17