Untitled

Abstract

The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of alpha-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewis(x), as well as the 2-(2-aminoethylthio)ethyl glycoside of alpha-D-mannopyranose, beta-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.

Synthetic Vaccines Consisting of Tumor‐Associated MUC1 Glycopeptide Antigens and Bovine Serum Albumin

“…In the case of glycopeptide 23 the coupling to furnish 25 proceeded more slowly, and led to the incorporation of only half as many antigen molecules. Furthermore, the glycopeptide antigen equipped with the spacer was covalently immobilized on microtiter plates38 functionalized with a secondary amine 26 (Scheme ). The covalent linkage of the MUC1 antigen to the microtiter plates (see 27 )39 prevents the loss of material in ELISA tests when washing with water, which had previously caused difficulties while working with glycopeptide antigens.…”

Printed covalent glycan array for ligand profiling of diverse glycan binding proteins

“…Each format differs in the type of glycans and the manner in which they are displayed. Some use noncovalent attachment to plastic or nitrocellulose membrane (6)(7)(8)(9)(10)(11)(12), and others use covalent attachment to plastic, gold, or glass (6,(13)(14)(15)(16)(17)(18)(19)(20). The glycans displayed range from a limited number of 5-45 exemplary structures representing terminal sequences on glycoprotein or glycolipid glycans (6,7,(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), to libraries of defined glycans, proteoglycan fragments, and microbial polysaccharides (8)(9)(10).…”

Synthetische Vakzine aus tumorassoziierten MUC1‐Glycopeptid‐Antigenen und Rinderserumalbumin

“…Beim Glycopeptid 23 verlief die Kupplung langsamer, sodass in 25 nur etwa halb so viele Antigenmoleküle an das Protein gebunden waren. Das mit dem Spacer ausgestattete Glycopeptid‐Antigen wurde zusätzlich kovalent auf mit sekundären Aminogruppen funktionalisierten Mikrotiterplatten der Struktur 26 38 immobilisiert (Schema ). Von diesen so überzogenen Mikrotiterplatten 27 39 kann das MUC1‐Antigen in den ELISA‐Tests mit Wasser nicht ausgewaschen werden, was bisher beim Arbeiten mit Glycopeptidantigenen stets zu Problemen geführt hatte.…”