76821-26-6

Upstream product

• 6401-81-6 maltotriose 
• 108-24-7 acetic anhydride 
• 6401-81-6 maltotriose 
• 6401-81-6 α-D-Glucopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)-β-D-glucopyranose 

Downstream Products

• 677031-70-8 2,3,6-tri-O-acetyl-4-O-(2,3,6-tri-D-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl phenylthiosulfonate 
• 291765-13-4 phenyl O-(α-D-glucopyranosyl-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 
• 426218-93-1 phenyl O-(4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 
• 478549-28-9 phenyl 4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltotrioside 
• 1448810-93-2 m-formyl-p-hydroxy-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 171411-99-7 allyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1<*>4)-O-α-D-glucopyranosyl-(1<*>4)-β-D-glucopyranoside 
• 250330-64-4 N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 250330-65-5 N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 426218-85-1 phenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-acetyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside 
• 426218-84-0 phenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-acetyl-1-thio-β-D-glucopyranoside 
• 426218-86-2 phenyl O-(α-D-glucopyranosyl-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside 
• 110519-31-8 pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 754201-87-1 2,4-dinitrophenyl α-maltotrioside 

Relevant academic research and scientific papers

Synthesis and mesomorphic properties of glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains: Part I. Synthesis

Glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated or chiral methyl branched chains in the tail and disaccharide and trisaccharide carbohydrate headgroups were synthesised. Standard procedures were used for the preparation of the educts and the glyco lipids: trichloracetimidate procedure for the preparation of long-chained compounds, glycosylation using the β-peracetate and boron trifluoride etherate was successful for the preparation of lipids with a medium-alkyl chain length. Preparation of the ester was afforded in a multi-step synthesis according to published procedures. Thus, several lipids were synthesised in a few synthetic steps in good yields. The introduction of unsaturated or methyl branched chains lead to liquid crystallinity at ambient temperature, because these compounds will be used as model compounds for biological systems. The biophysical properties of these compounds will be reported in a following paper.

Enhancing glycan stabilityviasite-selective fluorination: modulating substrate orientation by molecular design

Single site OH → F substitution at the termini of maltotetraose leads to significantly improved hydrolytic stability towards α-amylase and α-glucosidase relative to the natural compound. To explore the effect of molecular editing, selectively modified oli

Efficient regioselective chemical modifications of maltotriose: an easy access to oligosaccharidic scaffold

Regioselective chlorination of fully unprotected maltotriose has given in high yield 1I,2I-III,3I-III,4III-octa-O-acetyl-6I-III-trichloro-6I-III-trideoxymaltotriose. Moreover, regioselective ditritylation of methyl β-maltotrioside has provided the two regioselectively C6-disubstituted trisaccharides. Selective deprotection of these new compounds gives the corresponding diol and halogenated analogues, respectively, in good yield. All compounds have been completely characterized and the substitution pattern in the oligosaccharidic sequence has been elucidated. A new family of amphiphilic carbohydrates, namely the 6-deoxy-6-alkylthiomaltotriose derivatives, bearing either two or three thioalkyl hydrophobic chains, respectively, has been synthesized. Critical micellar concentration (CMC) values as well as the antimicrobial properties have been evaluated for amphiphilic compounds.

Maltotriose-based probes for fluorescence and photoacoustic imaging of bacterial infections

Currently, there are no non-invasive tools to accurately diagnose wound and surgical site infections before they become systemic or cause significant anatomical damage. Fluorescence and photoacoustic imaging are cost-effective imaging modalities that can be used to noninvasively diagnose bacterial infections when paired with a molecularly targeted infection imaging agent. Here, we develop a fluorescent derivative of maltotriose (Cy7-1-maltotriose), which is shown to be taken up in a variety of gram-positive and gram-negative bacterial strains in vitro. In vivo fluorescence and photoacoustic imaging studies highlight the ability of this probe to detect infection, assess infection burden, and visualize the effectiveness of antibiotic treatment in E. coli-induced myositis and a clinically relevant S. aureus wound infection murine model. In addition, we show that maltotriose is an ideal scaffold for infection imaging agents encompassing better pharmacokinetic properties and in vivo stability than other maltodextrins (e.g. maltohexose).

MALTOTRIOSE-BASED PROBES FOR FLUORESCENCE AND PHOTOACOUSTIC IMAGING OF BACTERIA

Embodiments of the present disclosure provide for labeled maltotriose probes, methods of making labeled probes, pharmaceutical compositions including labeled probes, methods of using labeled probes, methods of diagnosing, localizing, monitoring, and/or assessing bacterial infections, using labeled probes, kits for diagnosing, localizing, monitoring, and/or assessing bacterial infections, using labeled probes, and the like.

Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity

The development of entry inhibitors is an emerging approach to the inhibition of influenza virus. In our previous research, oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor. Herein, as a further study, we report the preparation of a series of OA-saccharide conjugates via the CuAAC reaction, and the anti-influenza activity of these compounds was evaluated in vitro. Among them, compound 11b, an OA-glucose conjugate, showed a significantly increased anti-influenza activity with an IC50 of 5.47 μM, and no obvious cytotoxic effect on MDCK cells was observed at 100 μM. Hemagglutination inhibition assay and docking experiment indicated that 11b might interfere with influenza virus infection by acting on HA protein. Broad-spectrum anti-influenza experiments showed 11b to be robustly potent against 5 different strains, including influenza A and B viruses, with IC50 values at the low-micromole level. Overall, this finding further extends the utility of OA-saccharide conjugates in anti-influenza virus drug design.

SACCHARIDE-LINKED CHLORIN DERIVATIVE

PROBLEM TO BE SOLVED: To provide an S-glycosylated chlorin derivative having excellent tumor cell killing properties (phototoxicity). SOLUTION: The S-glycosylated chlorin derivative is shown in the formula (X1-X4 are any group of F- or oligosaccharide-S-)

GLYCOSIDE COMPOUND

Compounds of formula (I″) wherein: R11, R12, R13, R14 and R15 are hydrogen, hydroxyl, C1-6 alkyl, C1-6 alkoxy, C1-6 alkyl-carbonyloxy, or a G-O— group, and at least one of R11, R12, R13, R14 and R15 is a G-O— group, wherein G is a saccharide residue,X1 is a single bond, or a methylene group, an ethylene group, a trimethylene group, a vinylene group or —CH═CH—CH2—,X2 is —CO—O— or —O—CO—,p and q are integer ofs 0 to 7, and p+q=0 to 8,Y1 is methylene, ethylene or an alkenylene group having a carbon number of 2 to 15 and 1 to 3 double bonds, andR16 and R17 are hydrogen, methyl or ethyl, or R16 and R17 form a C3-6 cycloalkyl group, are useful as GLP-1 secretion promoting agents.

A route to oligosaccharide-appended salicylaldehydes: Useful building blocks for the synthesis of metal-salophen complexes

A simple and general synthetic protocol to obtain oligosaccharide-appended salicylaldehydes, key intermediates for the synthesis of water-soluble metal-salophen complexes, is here reported. Six new aldehydes have been prepared and fully characterized as well as the corresponding zinc- and uranyl-salophen complexes. These new derivatives show very good solubility in water. Preliminary studies on the association of compound 19-U, that is, the uranyl maltotetraose derivative, with hydrogen phosphate and fluoride provide very encouraging results and open up the possibility of using such compounds for the efficient recognition of anions in pure water.

Saccharide-functionalized alkanethiols for fouling-resistant self-assembled monolayers: Synthesis, monolayer properties, and antifouling behavior

We describe the synthesis of a series of mono-, di-, and trisaccharide-functionalized alkanethiols as well as the formation of fouling-resistant self-assembled monolayers (SAMs) from these. The SAMs were characterized using ellipsometry, wetting measurements, and infrared reflection-absorption spectroscopy (IRAS). We show that the structure of the carbohydrate moiety affects the packing density and that this also alters the alkane chain organization. Upon increasing the size of the sugar moieties (from mono- to di- and trisaccharides), the structural qualities of the monolayers deteriorated with increasing disorder, and for the trisaccharide, slow reorganization dynamics in response to changes in the environmental polarity were observed. The antifouling properties of these SAMs were investigated through protein adsorption experiments from buffer solutions as well as settlement (attachment) tests using two common marine fouling species, zoospores of the green macroalga Ulva linza and cypris larvae of the barnacle Balanus amphitrite. The SAMs showed overall good resistance to fouling by both the proteins and the tested marine organisms. To improve the packing density of the SAMs with bulky headgroups, we employed mixed SAMs where the saccharide-thiols are diluted with a filler molecule having a small 2-hydroxyethyl headgroup. This method also provides a means by which the steric availability of sugar moieties can be varied, which is of interest for specific interaction studies with surface-bound sugars. The results of the surface dilution study and the low nonspecific adsorption onto the SAMs both indicate the feasibility of this approach.