One-pot high-throughput synthesis of beta-turn cyclic peptidomimetics via "volatilizable" supports.
A promising method for the high-throughput synthesis of linear C-hydroxyalkylamido peptidomimetics and beta-turn cyclic peptidomimetics via "volatilizable" aminoalkyl functionalized silica gels is presented. Boc amino acids and carboxylic acids were coupled on functionalized aminoalkyl silica gels using a standard DIC/HOBt coupling protocol. After peptide synthesis, the resin bound peptide was cleaved using a two-step process to obtain the linear C-hydroxyalkylamido peptidomimetics. Beta-turn cyclic peptidomimetics were generated by intramolecular S(N)Ar cyclization in an aqueous solution. Both the linear and the cyclic peptidomimetics were obtained with good to excellent yields and purities through a "one-pot" reaction.
Li
Yangmei
Y
Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port Saint Lucie, Florida 34987, USA.
Yu
Yongping
Y
Giulianotti
Marc
M
Houghten
Richard A
RA
D008968:Molecular Conformation; D018716:Molecular Mimicry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010456:Peptides, Cyclic