138332-00-0Relevant articles and documents
Chemo-Enzymatic Synthesis of S. mansoni O-Glycans and Their Evaluation as Ligands for C-Type Lectin Receptors MGL, DC-SIGN, and DC-SIGNR
Achilli, Silvia,Bernardi, Anna,Cioce, Anna,Fieschi, Franck,Goti, Giulio,Hernandez, Alvaro,Pham, Julie,Reichardt, Niels-Christian,Thepaut, Michel,Vivès, Corinne
, p. 12818 - 12830 (2020)
Due to their interactions with C-type lectin receptors (CLRs), glycans from the helminth Schistosoma mansoni represent promising leads for treatment of autoimmune diseases, allergies or cancer. We chemo-enzymatically synthesized nine O-glycans based on th
The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
Chaveriat, Ludovic,Stasik, Imane,Demailly, Gilles,Beaupere, Daniel
, p. 1349 - 1354 (2006)
6-Azido-6-deoxy-d-galactitol and d-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6-deoxy-d-hexono-1,4-lactones, and 6-azido-6-deoxy-d-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-d-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-d-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields.
Importance of topology for glycocluster binding to Pseudomonas aeruginosa and Burkholderia ambifaria bacterial lectins
Ligeour, Caroline,Dupin, Lucie,Angeli, Anthony,Vergoten, Gérard,Vidal, Sébastien,Meyer, Albert,Souteyrand, Eliane,Vasseur, Jean-Jacques,Chevolot, Yann,Morvan, Fran?ois
, p. 11244 - 11254 (2015)
Pseudomonas aeruginosa (PA) and Burkholderia ambifaria (BA) are two opportunistic Gram negative bacteria and major infectious agents involved in lung infection of cystic fibrosis patients. Both bacteria can develop resistance to conventional antibiotherap
FRET-based direct and continuous monitoring of human fucosyltransferases activity: An efficient synthesis of versatile GDP-L-fucose derivatives from abundant D-galactose
Maeda, Takahiro,Nishimura, Shin-Ichiro
, p. 478 - 487 (2008)
We have developed a facile and versatile protocol for the continuous monitoring of human fucosyltransferases activity by using fluorescence energy resonance transfer (FRET), and have explored the feasibility of its use in an inhibitor screening assay. A convenient sugar nucleotide with a fluorogenic probe, 6-deoxy-6-N-(2-naphalene-2-yl-acetamide)-β-L-galactopyranos-1-yl- guanosine 5′-diphosphate disodium salt (1), was efficiently synthesized from naturally abundant D-galactopyranose via a key intermediate, 6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-L-galactopyranose (10). It was demonstrated that the combined use of the glycosyl donor 1 and a dansylated acceptor substrate, sialyl-α2,3-LacNAc derivative (2) allowed us to carry out highly sensitive, direct, and continuous in vitro monitoring of the generation of sialyl Lewis X (SLex), which is catalyzed by human α1-,3-fucosyltransferase VI (FUT-VI). A kinetic analysis revealed that compound 1 was an excellent donor substrate (KM = 0.94 μM and Kmax = 0.14 μM min-1) for detecting human FUT-VI activity. To the best of our knowledge, this synthetic fluorogenic probe is the most sensitive and selective donor substrate for FUT-VI among all of the known GDP-Fuc analogues, including the parent GDP-Fuc. When a dansylated asparagine-linked glycopeptide 20, which is derived from egg yolk was employed as an alternate acceptor substrate, a FRET-based assay with compound 1 could be used to directly monitor the α1,6-fucosylation at the reducing terminal GlcNAc residue by human FUT-VIII (KM = 175 μM and Vmax = 0.06 μM/min); this indicates that the present method might become a general protocol for the characterization of various mammalian fucosyltransferases in the presence of designated fluorogenic acceptor substrates. The present protocol revealed that compound 23, which was obtained by a 1,3-dipolar cycloaddition between the disodium salt 16 and 1-ethynylnaphthalene exhibits highly potent inhibitory effects against the FUT-VI-mediated sialyl Lewis X synthesis (IC 50 = 5.4 μM).
Curdlan as a polymeric starting material to access C6-modified glucose derivatives
Miyazawa, Tomoyuki,Abe, Haruka,Suzuki, Takayuki,Togashi, Yosuke,Koshiji, Kazuhiro,Nonaka, Yuki,Hasegawa, Teruaki
, p. 252 - 266 (2014)
We evaluated the potential of a linear β-1,3-glucan (curdlan) as a starting material to access C6-modified glucose derivatives and found that 6-bromo-6-deoxyglucose, 6-azide-6-deoxyglucose, and 6-acetamido-6-deoxyglucose could be readily prepared from curdlan through its C6-selective and quantitative modifications and subsequent acid-catalyzed hydrolysis.
6-Azido d-galactose transfer to N-acetyl-d-glucosamine derivative using commercially available β-1,4-galactosyltransferase
Bosco, Micha?l,Gall, Sophie Le,Rihouey, Christophe,Couve-Bonnaire, Samuel,Bardor, Muriel,Lerouge, Patrice,Pannecoucke, Xavier
, p. 2294 - 2297 (2008)
A new strategy to tag glycoproteins carrying terminal GlcNAc was developed using commercially available bovine β-1,4-galactosyltransferase (GalT) and UDP-6-azidogalactose. The azide function was then allowed to react via a biotinylated Staudinger-Bertozzi probe demonstrating the usefulness of such a procedure to tag any glycoprotein possessing a N-acetylglucosamine terminal residue from any type of cell lysate.
Metallization of double-stranded DNA triggered by bound galactose-modified naphthalene diimide
Komizo, Kohei,Ikedo, Hideyuki,Sato, Shinobu,Takenaka, Shigeori
, p. 1547 - 1555 (2014)
Naphthalene diimide (NDI) derivatives bearing galactose moieties through different spacers, NDI-DS1 and NDI-DS2, were synthesized by the click reaction of the acetylene derivatives of NDI with galactose azide. They bound to double-stranded DNA with threading intercalation, as confirmed by the topoisomerase I assay and circular dichroism spectroscopy. The binding affinities of these ligands were on the order of 105 M-1 with several-fold higher affinity for double-stranded DNA than for single-stranded DNA. The silver mirror reaction on the double-stranded DNA bound to these ligands afforded silver nanowires that were converted to gold nanowires. In the atomic force microscopy measurements, the increased height of DNA areas on a mica plate was observed in the case of double-stranded DNA after NDI-DS2 treatment and subsequently silver mirror reaction, whereas the increased height of DNA areas was not observed in the case of single-stranded DNA after the same treatment.
Introducing Glycolinkers for the Functionalization of Cytotoxic Drugs and Applications in Antibody–Drug Conjugation Chemistry
Ekholm, Filip S.,Pynn?nen, Henna,Vilkman, Anja,Pitk?nen, Virve,Helin, Jari,Saarinen, Juhani,Satomaa, Tero
, p. 2501 - 2505 (2016)
Antibody–drug conjugates (ADCs) are promising alternatives to naked antibodies for selective drug-delivery applications and treatment of diseases such as cancer. Construction of ADCs relies upon site-selective, efficient and mild conjugation technologies.
Novel 1,2,3-triazole-tethered Pam3CAG conjugates as potential TLR-2 agonistic vaccine adjuvants
Mhamane, Tukaram B.,Sambyal, Shainy,Vemireddy, Sravanthi,Khan, Imran A.,Shafi, Syed,Halmuthur M., Sampath Kumar
, (2021)
A focused library of water soluble 1,2,3-triazole tethered glycopeptide conjugates derived from variety of azido-monosaccharides and aliphatic azido-alcohols were synthesized through manipulation at the C-terminus of Pam3CAG and screened for their potential as TLR2 agonistic adjuvants against HBsAg antigen. In vitro ligand induced TLR2 signal activation was observed with all the analogues upon treatment with HEK blue TLR2 cell lines. Conjugate derived from ribose (6e), which exhibited pronounced HBsAg specific antibody (IgG) titer also shown enhanced CD8+ population indicating superior cell mediated immunity compared to standard adjuvant Pam3CSK4. Further, docking studies revealed ligand induced heterodimerization between TLR1 and 2. Overall, the result indicates the usefulness of novel conjugates as potential vaccine adjuvant.
Site-Selective Chemoenzymatic Modification on the Core Fucose of an Antibody Enhances Its FcγReceptor Affinity and ADCC Activity
Li, Chao,Chong, Gene,Zong, Guanghui,Knorr, David A.,Bournazos, Stylianos,Aytenfisu, Asaminew Haile,Henry, Grace K.,Ravetch, Jeffrey V.,Mackerell, Alexander D.,Wang, Lai-Xi
, p. 7828 - 7838 (2021/05/26)
Fc glycosylation profoundly impacts the effector functions of antibodies and often dictates an antibody's pro- or anti-inflammatory activities. It is well established that core fucosylation of the Fc domain N-glycans of an antibody significantly reduces i
