Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites.
A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.
Li
Xuechen
X
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China. xuechenl@hku.hk
Lam
Hiu Yung
HY
Zhang
Yinfeng
Y
Chan
Chun Kei
CK
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D010455:Peptides / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013379:Substrate Specificity; D013912:Threonine / Q000737:chemistry*
D000447:Aldehydes; D010455:Peptides; C013243:salicylaldehyde; D013912:Threonine; D012694:Serine