Efficient sequential segment coupling using N-alkylcysteine-assisted thioesterification for glycopeptide dendrimer synthesis.
A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted thioesterification. The glycopeptide having C-terminal NAC was prepared by the Fmoc method and converted to the thioester by 3-mercaptopropionic acid treatment. The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, which was then converted to the thioester. Two tetramers were condensed with ethylenediamine to give the octameric glycopeptide dendrimer.
Ozawa
Chinatsu
C
Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Kanagawa 259-1292, Japan.
Katayama
Hidekazu
H
Hojo
Hironobu
H
Nakahara
Yuko
Y
Nakahara
Yoshiaki
Y
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry*; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D050091:Dendrimers; D004952:Esters; D006020:Glycopeptides; D013438:Sulfhydryl Compounds; D003545:Cysteine