Synthesis of all-L cyclic tetrapeptides using pseudoprolines as removable turn inducers.
Cyclic tetrapeptides have generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.
Fairweather
Kelly A
KA
School of Chemistry, The University of Sydney, 2006 NSW, Australia.
Sayyadi
Nima
N
Luck
Ian J
IJ
Clegg
Jack K
JK
Jolliffe
Katrina A
KA
D008958:Models, Molecular; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
D009842:Oligopeptides; D010456:Peptides, Cyclic; D013844:Thiazoles; C505976:pseudoproline; D011392:Proline