TY - JOUR
T1 - Oligosaccharide-Peptide Ligation of Glycosyl Thiolates with Dehydropeptides
T2 - Synthesis of S-Linked Mucin-Related Glycopeptide Conjugates
AU - Galonić, Danica P.
AU - Van Der Donk, Wilfred A.
AU - Gin, David Y.
PY - 2003/12/15
Y1 - 2003/12/15
N2 - A chemoselective strategy for oligosaccharide-peptide ligation is described in which α-thio analogues of mucin-related glycoconjugates can be readily accessed through site-selective conjugate addition of complex oligosaccharide thiolates to dehydroalanine-containing peptides. The efficiency of the ligation is high-lighted by the rapid convergent assembly of thioisosteres of the four tumor-associated carbohydrate antigens, T N, T, STN, and 2,6-ST, as a pair of diastereoisomers at the newly formed cysteine stereocenter. The process proceeds in high yield and with complete retention of the α-anomeric configuration.
AB - A chemoselective strategy for oligosaccharide-peptide ligation is described in which α-thio analogues of mucin-related glycoconjugates can be readily accessed through site-selective conjugate addition of complex oligosaccharide thiolates to dehydroalanine-containing peptides. The efficiency of the ligation is high-lighted by the rapid convergent assembly of thioisosteres of the four tumor-associated carbohydrate antigens, T N, T, STN, and 2,6-ST, as a pair of diastereoisomers at the newly formed cysteine stereocenter. The process proceeds in high yield and with complete retention of the α-anomeric configuration.
KW - Carbohydrates
KW - Chemoselective ligation
KW - Dehydropeptide
KW - Glycopeptides
KW - Mucin
UR - http://www.scopus.com/inward/record.url?scp=0346732163&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0346732163&partnerID=8YFLogxK
U2 - 10.1002/chem.200305290
DO - 10.1002/chem.200305290
M3 - Article
C2 - 14679512
AN - SCOPUS:0346732163
SN - 0947-6539
VL - 9
SP - 5997
EP - 6006
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 24
ER -