197663-12-0Relevant academic research and scientific papers
An armed-disarmed approach for blocking aglycon transfer of thioglycosides
Li, Zhitao,Gildersleeve, Jeffrey C.
, p. 559 - 562 (2007)
Thioglycosides are used frequently as glycosyl donors and as mimetics of O-glycosides. While being very useful, thioglycosides are prone to a detrimental side reaction referred to as aglycon transfer. In this letter, it is shown that aglycon transfer can
In vitro synthesis of mucin-type O-glycans using saccharide primers comprising GalNAc-Ser and GalNAc-Thr residues
Sakura, Ryuma,Nagai, Kaori,Yagi, Yuka,Takahashi, Yoshihisa,Ide, Yoshimi,Yagi, Yuki,Yamamoto, Daiki,Mizuno, Mamoru,Sato, Toshinori
, (2022/01/14)
Mucin-type O-glycosylation of serine or threonine residue in proteins is known to be one of the major post-translational modifications. In this study, two novel alkyl glycosides, Nα-lauryl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serineamide (GalNAc-Ser-C12) and Nα-lauryl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonineamide (GalNAc-Thr-C12) were synthesized as saccharide primers to prime mucin-type O-glycan biosynthesis in cells. Upon incubating human gastric cancer MKN45 cells with the saccharide primers, 22 glycosylated products were obtained, and their structures were analyzed using liquid chromatography-mass spectrometry and enzyme digestion. The amounts of glycosylated products were dependent on the amino acid residues in the saccharide primers. For example, in vitro synthesis of T antigen (Galβ1-3GalNAc), fucosyl-T (Fucα1-2Galβ1-3GalNAc), and sialyl-T (NeuAcα2-3Galβ1-3GalNAc) preferred a serine residue, whereas sialyl-Tn (NeuAcα2-6GalNAc) preferred a threonine residue. Furthermore, the glycosylated products derived from GalNAc-Ser/Thr-C12 and Gal-GalNAc-Ser/Thr-C12 using cell-free synthesis showed the same amino acid selectivity as those in the cell experiments. These results indicate that glycosyltransferases involved in the biosynthesis of mucin-type O-glycans distinguish amino acid residues conjugated to GalNAc. The saccharide primers developed in this study might be useful for comparing mucin-type oligosaccharides in cells and constructing oligosaccharide libraries to study cell function.
Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant
Bourgault, Jean Paul,Trabbic, Kevin R.,Shi, Mengchao,Andreana, Peter R.
supporting information, p. 1699 - 1702 (2014/03/21)
The α-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a d-GalN3 acceptor carrying a pre-installed α-N- hydroxysuccinimidyl moiety. The natural α linkage was prepar
GLYCOSYLATED ANTITUMOR ETHER LIPIDS AS NOVEL CANCER STEM CELL CYTOTOXIC AGENTS
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Page/Page column 36, (2013/08/28)
Glycosylated antitumor ether lipids (GAELs) are effective cytotoxic agents against cancer stem cells. Furthermore, combining GAELs which kill cells by a caspase-independent pathway with agents that kill cells by apoptosis will lead to elimination of the differentiated tumor cells and the undifferentiated cancer stem cells leading to an elimination of the tumor and preventing recurrence.
Total synthesis of lipoteichoic acid of streptococcus pneumoniae
Pedersen, Christian Marcus,Figueroa-Perez, Ignacio,Lindner, Buko,Ulmer, Artur J.,Zaehringer, Ulrich,Schmidt, Richard R.
scheme or table, p. 2585 - 2590 (2010/06/12)
"Chemical Equation Preseted" Mixed signals: The glycophospholipid 1, consisting of two cholinylphosphoCalNAc units, two 2-acetamino-4-amino2,4,6- trideoxygalactose rings, three glucose residues each with different linkages to other sugar units, and a ribitolphosphate residue, has been synthesized. Target 1 is recognized by the immune system, but not by the TLR-2 signaling receptor as previously postulated.
Mechanistic studies and methods to prevent aglycon transfer of thioglycosides
Li, Zhitao,Gildersleeve, Jeffrey C.
, p. 11612 - 11619 (2007/10/03)
Thioglycosides have been employed extensively for the synthesis of complex oligosaccharides, carbohydrate libraries, and mimetics of O-glycosides. While very useful, aglycon transfer is a problematic side reaction with thioglycosides. In this paper, a series of mechanistic studies are described. The aglycon transfer process is shown to affect both armed and disarmed thioglycosides, cause anomerization of the carbon-sulfur bond of a thioglycoside, and destroy the product of a glycosylation reaction. The results indicate that the aglycon transfer process can be a major problem for a wide range of thioglycosides. This side reaction is especially important to consider when carrying out complex reactions such as solid-phase glycosylations, one-pot or orthogonal multicomponent glycosylations, and construction of carbohydrate libraries. To prevent transfer, a number of modified aglycons were examined. The 2,6-dimethylphenyl (DMP) aglycon was found to effectively block transfer in a variety of model studies and glycosylation reactions. The DMP group can be installed in one step from a commercially available thiol (2,6- dimethylthiophenol) and is useable as a glycosyl donor. On the basis of these features, the DMP group is proposed as a convenient and improved aglycon for thioglycosides.
Synthesis of Tn, and sialyl Tn antigen-lipid a analog conjugates for synthetic vaccines
Miyajima, Keisuke,Nekado, Takahiro,Ikeda, Kiyoshi,Achiwa, Kazuo
, p. 1544 - 1546 (2007/10/03)
Conjugates of Tn and sialyl Tn antigen with N-teradecanoyl L-seryl-β- alanine-containing 9-glucosamine derivatives structurally related to lipid A as a immunoadjuvant were synthesized for the development of totally synthetic vaccines against cancers or HIV.
