A short synthesis of bicyclic dipeptides corresponding to Xxx-L-Pro Xxx-D-Pro having constrained trans-proline amides.
[formula: see text] A short synthesis that generates two isomeric bicyclic dipeptides having constrained, trans-proline amide bonds has been developed. One of these bicyclic dipeptides corresponds to an Xxx-L-Pro dipeptide (4), while the other isomer corresponds to an Xxx-D-Pro dipeptide (5). The two isomers are readily distinguished by their 1H NMR spectra.
Curran
T P
TP
Department of Chemistry, College of the Holy Cross, Worcester, Massachusetts 01610-2395, USA. tcurran@holycross.edu
Marcaurelle
L A
LA
O'Sullivan
K M
KM
D000577:Amides / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*
D000577:Amides; D004151:Dipeptides; D010456:Peptides, Cyclic; D011392:Proline