Azopeptides: Synthesis and Pericyclic Chemistry.
Azopeptides possess an imino urea as an amino amide surrogate in the sequence. Azopeptides were synthesized by oxidation of aza-glycine residues and employed in pericyclic chemistry. Diels-Alder cyclizations and Alder-ene reactions on azopeptides enabled construction of constrained aza-pipecolyl and reactive aza-allylglycyl residues. X-ray crystallographic analyses of azopeptide 16a and azapeptides 30a and 35a provided insight into imino urea configuration and conformational affects of cycloalkane side chains at the semicarbazide α- and β-nitrogen, respectively.
Département de Chimie, Université de Montréal , C.P. 6128, Succursale Centre-Ville, Montréal, Québec Canada H3C 3J7.
Ramesh
R
Chingle
Département de Chimie, Université de Montréal , C.P. 6128, Succursale Centre-Ville, Montréal, Québec Canada H3C 3J7.
William D
WD
Lubell
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D005998:Glycine / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D012663:Semicarbazides / Q000737:chemistry
D001391:Azo Compounds; D010455:Peptides; D012663:Semicarbazides; C010059:carbamylhydrazine; D005998:Glycine