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

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 subse...

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Bibliographic Details
Published in:Tetrahedron 2010-07, Vol.66 (29), p.5357-5366
Main Authors: van Lierop, Bianca J., Jackson, W. Roy, Robinson, Andrea J.
Format: Article
Language:English
Subjects:
5,5-Dimethyl- l-proline
Acid-catalysed cyclisation
Cisoidal amide bond
Cis–trans isomerisation
Cross metathesis (CM)
Pseudoproline residues
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Summary: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. An acid-stable class of cisoidal amide bond-promoting 5,5-dimethyl- l-proline dipeptides has been developed for direct insertion into linear peptide sequences. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.05.068