83956-33-6

Upstream product

• 21209-51-8 N-benzyloxycarbonyl-L-serine benzyl ester 
• 167939-15-3 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate 
• 183801-48-1 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(pyridin-2-ylsulfanylcarbonyloxy)-tetrahydro-pyran-4-yl ester 
• 83025-11-0 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate 
• 21209-51-8 N-(Benzyloxycarbonyl)-L-serin-benzylester 
• 110797-30-3 Ethyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-1-thio-β-D-galactopyranosid 
• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 

Downstream Products

• 17041-36-0 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-serin 
• 83956-37-0 3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester 
• 60280-57-1 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine 

Relevant academic research and scientific papers

Stereoselective synthesis of natural and non-natural thomsen-nouveau antigens and hydrazide derivatives

A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to α- or β-anomers in excellent yields (72-96%) and selectivity (～100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant

The efficient chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant is demonstrated under transglycosylation conditions employing β-galactosidase from bovine testes.

Synthesis of clustered D-GalNAc (Tn) and D-Galβ(1→3)GalNAc (T) antigenic motifs using a pentaerythritol scaffold

The tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Galβ(1→3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective α-glycolyl and α-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate antigens and vaccines.

SYNTHETIC VACCINES: I. SYNTHESIS OF MULTIVALENT Tn ANTIGEN CLUSTER-LYSYLLYSINE CONJUGATES

Monomer, dimer, and trimer of Tn antigen (GalNAcα1-O-Ser) were coupled to L-lysyllysine to construct multivalent and clustering structures of Tn antigen.The method has made it possible to provide pertinent carbohydrate antigens for the development of synthetic vaccines against tumors.

Building Units of Oligosaccharides, LXXXVI1). - Glycosidation with Thioglycosides of Oligosaccharides to Segments of O-Glycoproteins.

In the presence of dimethyl(methylthio)sulfonium triflate (DMTST) thioglycosides of mono-, di-, tri-, and tetrasaccharides, which contain a 2-azido-2-deoxy-D-galactose as reducing unit, can react with the hydroxy group of selectively blocked derivatives of L-serine.These reactions yield the corresponding O-glycosides.Preferentially the α-glycosidically bound products will be obtained.In this way the trisaccharide glycoside 46 was prepared, which represents the core-II structure of mucins α-glycosidically linked to L-serine.Methyl triflate as promoter of this thioglycosidation is less efficient than DMTST.