127753-65-5Relevant academic research and scientific papers
Synthesis of a tumor-associated 2,3-sialyl-T glycododecapeptide antigen from the tandem repeat region of the mucin MUC1
Dziadek, Sebastian,Kunz, Horst
, p. 1623 - 1626 (2003)
As a cell surface antigen for the development of selective antitumor vaccines, a tumor-associated glycododecapeptide from epithelial MUC1 carrying the 2,3-sialyl-T antigen was synthesized. The 2,3-ST building block was assembled from a TN-threo
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
supporting information, p. 12939 - 12945 (2019/08/22)
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity
Stra?burger, David,Glaffig, Markus,Stergiou, Natascha,Bialas, Sabrina,Besenius, Pol,Schmitt, Edgar,Kunz, Horst
, p. 1142 - 1146 (2018/10/21)
The endothelial glycoprotein MUC1 is known to underlie alterations in cancer by means of aberrant glycosylation accompanied by changes in morphology. The heavily shortened glycans induce a collapse of the peptide backbone and enable accessibility of the latter to immune cells, rendering it a tumor-associated antigen. Synthetic vaccines based on MUC1 tandem repeat motifs, comprising tumor-associated 2,3-sialyl-T antigen, conjugated to the immunostimulating tetanus toxoid, are reported herein. Immunization with these vaccines in a simple water/oil emulsion produced a strong immune response in mice to which stimulation with complete Freund’s adjuvant (CFA) was not superior. In both cases, high levels of IgG1 and IgG2a/b were induced in C57BL/6 mice. Additional glycosylation in the immunodominant PDTRP domain led to improved binding of the induced antisera to MCF-7 breast tumor cells, compared with that of the monoglycosylated peptide vaccine.
1,2;3,4-Di-O-isopropylidene-l-galactose synthesis from its d-enantiomer
Doboszewski, Bogdan,Herdewijn, Piet
, p. 2253 - 2256 (2012/05/20)
Easy procedure was devised to obtain di-O-isopropylidene-l-galactose from di-O-isopropylidene-d-galactose.
Modifying the regioselectivity of glycosynthase reactions through changes in the acceptor
Stick, Robert V.,Stubbs, Keith A.,Watts, Andrew G.
, p. 779 - 786 (2007/10/03)
Successful glycosynthase-mediated reactions have been performed on 6-O-benzyl-, 6-O-(4-nitrobenzyl)-, and 6-O-benzoyl-D-glucopyranose to give 1,2-β- and 1,3-β-D-glycosylated products; 4-O-benzyl-D-xylopyranose gave only a 1,2-β-glycosylated product. A rat
Syntheses of novel photoaffinity probes for bioorganic studies on nyctinasty of leguminous plants
Sugimoto, Takanori,Fujii, Tomohiko,Hatanaka, Yasumaru,Yamamura, Shosuke,Ueda, Minoru
, p. 6529 - 6532 (2007/10/03)
Novel and non-radioactive photoaffinity probes (1 and 2) for the bioorganic study of nyctinasty are designed and synthesized based on potassium isolespedezate (3), which induce leaf-opening against the leaf of Cassia mimosoides L. These probes bear a trifluoromethyldiazirine or diazophenyl group for photoaffinity and a biotin subunit for affinity chromatography and chemiluminescent detection. Probes (1 and 2) showed leaf-opening activity at 5×10-5 mol/L with leaves of C. mimosoides; thus, they would be an important tool for the identification of a receptor protein for 3.
An economical synthesis of Lewis X, sialyl lewis X and their α-galactosyl analogues
Dekany, Gyula,Wright, Karen,Toth, Istvan
, p. 983 - 999 (2007/10/03)
Economical syntheses of the Lewis X trisaccharide 8 and sialyl Lewis X tetrasaccharide 18 epitopes and the syntheses of the α-galactosyl epimers 9 and 20 of these structures are described. Thioglycosides 2, 5, 11 and 15 were used as glycosyl donors to con
Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners
Danishefsky, Samuel J.,Gervay, Jacquelyn,Peterson, John M.,McDonald, Frank E.,Koseki, Koshi,Griffith, David A.,Oriyama, Takeshi,Marsden, Stephen P.
, p. 1940 - 1953 (2007/10/02)
Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLex tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The us
Synthesis of phosphoric acid diesters of 7β-hydroxycholesterol and of carbohydrates
Pannecoucke, Xavier,Schmitt, Gaby,Luu, Bang
, p. 6569 - 6578 (2007/10/02)
In order to enhance the antitumor efficacy of 7β-hydroxycholesterol by targeting its action to defined organs, the phosphoric acid esters of 3(7β-hydroxycholesteryl) and of 6(galactopyranosyl) 1 or 6(mannopyranosyl) 2 were synthesized by the phosphoramidi
STEREOCHEMICAL VARIATIONS IN AQUEOUS CYCLOADDITIONS USING GLYCO-ORGANIC SUBSTRATES AS A CONSEQUENCE OF CHEMICAL MANIPULATIONS ON THE SUGAR MOIETY
Lubineau, Andre,Queneau, Yves
, p. 6697 - 6712 (2007/10/02)
Chemical modifications of the sugar moiety in dienyl glycosides allowed us to rationalize the stereochemistry of our aqueous cycloadditions using glyco-organic substrates.In this way, several dienyl glucosides having benzyl group in 2 or 6 position of the
