106256-81-9Relevant academic research and scientific papers
Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors
Dean, Barbara,Oguchi, Hisao,Cai, Shaopei,Otsuji, Eigo,Tashiro, Kazuhiro,et al.
, p. 175 - 192 (1993)
A β-lactosyl residue was linked to the amino groups of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C9) to give trivalent β-lactosyl clusters in order to increase the inhibitory activity of the β-lactosyl group against tumo
Multivalent scaffolds induce galectin-3 aggregation into nanoparticles
Goodman, Candace K.,Wolfenden, Mark L.,Nangia-Makker, Pratima,Michel, Anna K.,Raz, Avraham,Cloninger, Mary J.
, p. 1570 - 1577 (2014)
Galectin-3 meditates cell surface glycoprotein clustering, cross linking, and lattice formation. In cancer biology, galectin-3 has been reported to play a role in aggregation processes that lead to tumor embolization and survival. Here, we show that lactose-functional-ized dendrimers interact with galectin-3 in a multivalent fashion to form aggregates. The glycodendrimer-galectin aggregates were characterized by dynamic light scattering and fluorescence microscopy methodologies and were found to be discrete particles that increased in size as the dendrimer generation was increased. These results show that nucleated aggregation of galectin-3 can be regulated by the nucleating polymer and provide insights that improve the general understanding of the binding and function of sugar-binding proteins.
Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose
Moynihan, Humphrey A.,Hayes, John A.,Eccles, Kevin S.,Coles, Simon J.,Lawrence, Simon E.
, p. 29 - 39 (2013)
A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P21 space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P21 space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R33 (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P212121 space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P21 space group and featured the primary amide groups forming R23(8) motifs generating a 2 1 ladder.
Synthesis and anticoagulant activity of polyureas containing sulfated carbohydrates
Huang, Yongshun,Shaw, Maureen A.,Mullins, Eric S.,Kirley, Terence L.,Ayres, Neil
, p. 4455 - 4466 (2014)
Polyurea-based synthetic glycopolymers containing sulfated glucose, mannose, glucosamine, or lactose as pendant groups have been synthesized by step-growth polymerization of hexamethylene diisocyanate and corresponding secondary diamines. The obtained pol
The design and synthesis of an α-Gal trisaccharide epitope that provides a highly specific anti-Gal immune response
Anraku, Kensaku,Sato, Shun,Jacob, Nicholas T.,Eubanks, Lisa M.,Ellis, Beverly A.,Janda, Kim D.
, p. 2979 - 2992 (2017)
Carbohydrate antigens displaying Galα(1,3)Gal epitopes are recognized by naturally occurring antibodies in humans. These anti-Gal antibodies comprise up to 1% of serum IgG and have been viewed as detrimental as they are responsible for hyperacute organ rejections. In order to model this condition, α(1,3)galactosyltransferase-knockout mice are inoculated against the Galα(1,3)Gal epitope. In our study, two α-Gal trisaccharide epitopes composed of either Galα(1,3)Galβ(1,4)GlcNAc or Galα(1,3)Galβ(1,4)Glc linked to a squaric acid ester moiety were examined for their ability to elicit immune responses in KO mice. Both target epitopes were synthesized using a two-component enzymatic system using modified disaccharide substrates containing a linker moiety for coupling. While both glycoconjugate vaccines induced the required high anti-Gal IgG antibody titers, it was found that this response had exquisite specificity for the Galα(1,3)Galβ(1,4)GlcNAc hapten used, with little cross reactivity with the Galα(1,3)Galβ(1,4)Glc hapten. Our findings indicate that while homogenous glycoconjugate vaccines provide high IgG titers, the carrier and adjuvanting factors can deviate the specificity to an antigenic determinant outside the purview of interest.
Preparation of linear oligosaccharides by a simple monoprotective chemo-enzymatic approach
Filice, Marco,Palomo, Jose M.,Bonomi, Paolo,Bavaro, Teodora,Fernandez-Lafuente, Roberto,Guisan, Jose M.,Terreni, Marco
, p. 9286 - 9292 (2008)
A monoprotective approach, involving acetyl ester as unique protective group in oligosaccharides synthesis, has been developed. Starting from peracetylated monosaccharides and glycals, by using an efficient and selective chemo-enzymatic 'one-pot' strategy (a regioselective hydrolysis catalyzed by immobilized lipases followed by a chemical acyl migration), different carbohydrate acceptors, only protected with acetyl ester, can be achieved. If combined with the use of an acetylated glycosyl donor, the glycosylation reaction with these glycosyl acceptors leads to peracetylated oligosaccharides. These compounds can be directly used as intermediates for the synthesis of glycopeptides used as antitumoral vaccines and, at the end of the process, can be easily fully deprotected in only one step. Thus, these key building blocks have been successfully used in glycosylation reactions for an efficient construction of peracetylated disaccharides, such as the biological relevant lactosamine, in multigram scale. Subsequently, glycosylation with the 3OH-tetraacetyl-α-d-galactose, used as carbohydrate acceptor, allowed the synthesis of a peracetylated N-trisaccharidic precursor of the lacto-N-neo-tetraose antigen. Extending this strategy to a 3OH-di-acetyl galactal, one peracetylated precursor of the T tumor-associated carbohydrate antigen has been synthesized. This efficient approach, characterized by the use of the acetyl ester as only protecting group during all the synthetical steps expected, represents an easy and efficient alternative to the classical synthetic methods in carbohydrate chemistry that involve several protecting group manipulation.
Effect of distal sugar and interglycosidic linkage of disaccharides on the activity of proline rich antimicrobial glycopeptides
Lele, Deepti S.,Dwivedi, Rohini,Kumari, Saroj,Kaur, Kanwal J.
, p. 833 - 844 (2015)
The effect of glycosylation on protein structure and function depends on a variety of intrinsic factors including glycan chain length. We have analyzed the effect of distal sugar and interglycosidic linkage of disaccharides on the properties of proline-ri
Deprotection-Induced Micellization of Glycopolymers: Control of Kinetics and Morphologies
Wu, Xiulong,Su, Lu,Chen, Guosong,Jiang, Ming
, p. 3705 - 3712 (2015)
In recent years, self-assembly of block or graft copolymers with sugar-containing component has drawn great attention. We just reported that protection-deprotection chemistry could initiate self-assembly of glycopolymers based on the high polarity change
Preparation of carbohydrate-oligonucleotide conjugates using the squarate spacer
Yan, Hongbin,Aguilar, Aime Lopez,Zhao, Yuyan
, p. 6535 - 6538 (2007)
Attachment of carbohydrates to oligonucleotides has proven to induce receptor-mediated endocytosis. A facile method for the formation of covalent linkages between glycans and oligonucleotides is herein described. Thus, use of 3,4-diethoxy-3-cyclobutene-1,2-dione as a linking reagent provides easy conjugation between carbohydrates bearing an amino group at the reducing end and oligonucleotides bearing an aminoalkyl modification.
Probing the lactose·GM3 carbohydrate - Carbohydrate interaction with glycodendrimers
Seah, Nicole,Santacroce, Paul V.,Basu, Amit
, p. 559 - 562 (2009)
(Figure Presented) Multivalent glycoconjugates were prepared using generation-4 PAMAM dendrimers, and their interaction with Langmuir monolayers containing GM3 was investigated. Excessive carbohydrate valency adversely affects the carbohydrate-carbohydrate interaction. The GM3 monolayer selectively interacts with lactose-functionalized dendrimers in the presence of calcium ions.
