Abstract
The synthesis of three neoglycopeptides incorporating carbohydrate haptens, differing in length, covalently linked to a non natural universal T helper peptide is disclosed. They were synthesized according to a blockwise strategy based on the condensation of appropriate di-, tri-, and tetrasaccharide trichloroacetimidate donors onto an azidoethyl 2-acetamido-2-deoxybeta-D-glucopyranoside acceptor. Use of thiol-maleimide coupling chemistry allowed site-selective efficient conjugation.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Acetylglucosamine / chemistry
-
Antigens, Bacterial / chemistry
-
Carbohydrate Conformation
-
Epitopes, B-Lymphocyte / chemistry
-
Epitopes, T-Lymphocyte / chemistry
-
Glucose / chemistry
-
Glycoconjugates / chemical synthesis*
-
Glycoconjugates / immunology
-
Glycopeptides / chemical synthesis
-
Glycosylation
-
Lipopolysaccharides / chemistry
-
Lysine / chemistry
-
Magnetic Resonance Spectroscopy
-
Malaria Vaccines / chemistry*
-
Molecular Structure
-
O Antigens / chemistry*
-
Oligosaccharides / chemical synthesis
-
Oligosaccharides, Branched-Chain / chemical synthesis
-
Rhamnose / chemistry
-
Shigella flexneri / immunology*
-
Vaccines, Conjugate / chemistry*
-
Vaccines, Conjugate / immunology
-
Vaccines, Synthetic / chemistry
Substances
-
Antigens, Bacterial
-
Epitopes, B-Lymphocyte
-
Epitopes, T-Lymphocyte
-
Glycoconjugates
-
Glycopeptides
-
Lipopolysaccharides
-
Malaria Vaccines
-
O Antigens
-
Oligosaccharides
-
Oligosaccharides, Branched-Chain
-
PADRE 45
-
Vaccines, Conjugate
-
Vaccines, Synthetic
-
Glucose
-
Lysine
-
Rhamnose
-
Acetylglucosamine