69266-16-6

Usage

Chemical Properties

White to off-white powder

Upstream product

• 30854-62-7 lactosyl azide 
• 3616-19-1 lactose octaacetate 
• 5965-66-2 LACTOSE 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 

Downstream Products

• 252845-49-1 [3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranosyl azide 
• 562847-31-8 4',6'-O-benzylidene-β-lactopyranosyl azide 
• 884525-76-2 1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea 
• 884525-74-0 (6-{3-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-ureidomethyl}-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 383912-96-7 2-[2-(2-acetylamino-acetylamino)-4-(trityl-carbamoyl)-butyrylamino]-N-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-succinamic acid tert-butyl ester 
• 383912-94-5 N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-[N⁴-(β-D-galactopyranosyl-1,4-glucopyranosyl)]-L-asparagine tert-butyl ester 
• 226707-98-8 O-(3,4-O-isopropylidene-2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide 
• 226707-99-9 O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide 
• 1198402-03-7 1,4-di[1-(β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl)-1,2,3-triazol-4-ylmethyloxy]benzene 
• 30854-62-7 lactosyl azide 

Relevant academic research and scientific papers

GLYCOPOLYMER, METHOD OF PREPARATION THEREOF, USE THEREOF AS MEDICAMENT

The invention relates to multivalent glycopolymers based on HPMA polymers (copolymers or homopolymers) with carbohydrate structures containing a terminal monosaccharide in the galacto-configuration, which are effective as galectin inhibitors. These glycopolymers can be used as drugs for the therapy and prevention of oncological diseases associated with overproduction of galectins, especially of human galectin-3 (Gal-3).

Exploration of the Reactivity of Multivalent Electrophiles for Affinity Labeling: Sulfonyl Fluoride as a Highly Efficient and Selective Label

Here we explored the reactivity of a set of multivalent electrophiles cofunctionalized with a carbohydrate ligand on gold nanoparticles to achieve efficient affinity labeling for target protein analysis. Evaluation of the reactivity and selectivity of the electrophiles against three different cognate binding proteins identified arylsulfonyl fluoride as the most efficient protein-reactive group in this study. We demonstrated that multivalent arylsulfonyl fluoride probe 4 at 50 nm concentration achieved selective affinity labeling and enrichment of a model protein PNA in cell lysate, which was more effective than photoaffinity probe 1 with arylazide group. Labeling site analysis by LC–MS/MS revealed that the nanoparticle-immobilized arylsulfonyl fluoride group can target multiple amino acid residues around the ligand binding site of the target proteins. Our study highlights the utility of arylsulfonyl fluoride as a highly effective multivalent affinity label suitable for covalently capturing unknown target proteins.

Glycoprotein Mimics with Tunable Functionalization through Global Amino Acid Substitution and Copper Click Chemistry

Glycoproteins and their mimics are challenging to produce because of their large number of polysaccharide side chains that form a densely grafted protein-polysaccharide brush architecture. Herein a new approach to protein bioconjugate synthesis is demonst

Teaming up synthetic chemistry and histochemistry for activity screening in galectin-directed inhibitor design

A hallmark of endogenous lectins is their ability to select a few distinct glycoconjugates as counterreceptors for functional pairing from the natural abundance of cellular glycoproteins and glycolipids. As a consequence, assays to assess inhibition of le

Glycosidase activated release of fluorescent 1,8-naphthalimide probes for tumor cell imaging from glycosylated 'pro-probes'

Glycosylated 4-amino-1,8-naphthalimide derivatives possess a native glycosidic linkage that can be selectively hydrolysed in situ by glycosidase enzymes to release the naphthalimide as a fluorescent imaging or therapeutic agent. In vitro studies using a variety of cancer cell lines demonstrated that the naphthalimides only get taken up into cells upon enzymatic cleavage from the glycan unit; a mechanism that offers a novel approach for the targeted delivery of probes/drugs.

Multivalent effect of glycopolypeptide based nanoparticles for galectin binding

Synthetic glycopolypeptides are versatile glycopolymers used to conceive bioinspired nanoassemblies. In this work, novel amphiphilic glycopolypeptides were designed to incorporate lactose or galactan in order to prepare polymeric nanoassemblies with sizes below 50 nm. The bioactivity of the two different outer surface sugar units was evaluated by defining glycan relative binding affinities to human galectins 1 and 3. A specific multivalent effect was found only for polymeric nanoparticles displaying galactan with a significant increase of the binding activity as compared to free glycan in solution. Such synthetic designs present great potential as therapeutic tools to address galectin related pathologies.

Site-specific glycoconjugation of protein via bioorthogonal tetrazine cycloaddition with a genetically encoded trans -cyclooctene or bicyclononyne

Efficient access to proteins modified site-specifically with glycans is important in glycobiology and for therapeutic applications. Herein, we report a biocompatible protein glycoconjugation by inverse demand Diels-Alder reaction between tetrazine and tra

Synthesis of new saccharide azacrown cryptands

Abstract New cryptands including bis-azacrown and saccharidic moieties in their structure were prepared in several steps by applying Staudinger-aza-Wittig reaction (SAW). Syntheses have been started from cheap, easily available commercial compounds such as D-glucose, D-cellobiose and D-lactose subsequently transformed into their derivatives in fairly good yields (60-65%) and suitable to give desired final cryptands by direct SAW coupling reactions.

Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds

A combination of classical site-directed mutagenesis, genetic code engineering and bioorthogonal reactions delivered a chemically modified barstar protein with one or four carbohydrates installed at specific residues. These protein conjugates were employed in multivalent binding studies, which support the use of proteins as structurally defined scaffolds for the presentation of multivalent ligands.

A multifunctional Pasteurella multocida sialyltransferase: A powerful tool for the synthesis of sialoside libraries

A multifunctional sialyltransferase has been cloned from Pasteurella multocida strain P-1059 and expressed in E. coli as a truncated C-terminal His6-tagged recombinant protein (tPm0188Ph). Biochemical studies indicate that the obtained protein