Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides.
Despite the vast number of techniques developed for the cyclization of small peptides, cyclization efficiency remains problematic in peptides that lack turn-promoting structures. Here we demonstrate the utility of click chemistry as a macrocyclization tool in the solid-phase synthesis of cyclic tetra-, penta-, hexa-, and heptapeptides. On-resin cyclization is completed at room temperature within 6 h, resulting in predominantly monomer with small amounts of cyclomultimer byproducts.
Turner
Rushia A
RA
Department of Chemistry and Biochemistry, University of California at Santa Cruz, 1156 High Street, Santa Cruz, California 95064, USA.
Oliver
Allen G
AG
Lokey
R Scott
RS
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013997:Time Factors
D010456:Peptides, Cyclic