109215-53-4

Basic information

• Product Name: D-glucose pentaacetate
• CAS NO: 109215-53-4
• Molecular Weight: 390.344
• Mol File: 109215-53-4.mol
• Article Data: 301

Chemical Properties

• CAS DataBase Reference: D-glucose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: D-glucose pentaacetate(109215-53-4)
• EPA Substance Registry System: D-glucose pentaacetate(109215-53-4)

Safety Data

• Hazardous Substances Data: 109215-53-4(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 2280-44-6 D-Glucose 
• 64-19-7 acetic acid 
• 127-08-2 potassium acetate 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 127-09-3 sodium acetate 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 50-99-7 D-glucose 
• 75-36-5 acetyl chloride 
• 492-62-6 alpha-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-46-3 recorcinol 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 

Downstream Products

• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 
• 125354-48-5 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 37797-55-0 1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 6087-47-4 O³,O⁴,O⁶-triacetyl-O²-trichloroacetyl-β-D-mannopyranosyl chloride 
• 16977-78-9 2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 16977-78-9 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 488759-90-6 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-acetyl-3-cyano-4-(4-methoxy-phenyl)-6-methyl-pyridin-2-ylsulfanyl]-tetrahydro-pyran-3-yl ester 
• 488759-89-3 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-acetyl-4-(4-chloro-phenyl)-3-cyano-6-methyl-pyridin-2-ylsulfanyl]-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Assembly and inhibitory activity of monovalent mannosides terminated with aromatic methyl esters: The effect of naphthyl groups

A series of monovalent α-D-mannoside ligands terminated with aromatic methyl esters have been synthesized in excellent yields using the Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (“click chemistry”). These mannosides were designed to have a unique aglycone moiety (tail) that combines a triazole ring attached to aromatic methyl esters via a six carbon alkyl chain. The mannose unit of these ligands was linked at the ortho, meta, and para positions of substituted methyl benzoates and 1-, 3-, and 6-substituted methyl 2-napthaoates. In hemagglutination assays, ligands (32A-38A) showed better inhibitory activities than the standard inhibitor, methyl α-D-mannopyranoside. Overall, the naphthyl-based mannoside ligand (37A) showed the best activity and therefore merits further development.

Improved synthesis of per-O-acetylated C1 hydroxyglycopyranose and structural study as non-covalent organic framework

An improved method for the synthesis of per-O-acetylated C-1-hydroxyglycopyranose was developed by hydrolysis of per-O-acetylated glycopyranosyl α-chlorides derived from sugars with C-2 axial acetates for example l-rhamnose and d-mannose. 2,3,4-Tri-O-acetyl-α-l-rhamnopyranose crystallized in tetragonal space group I4, a rare phenomenon in carbohydrate literature. The three dimensional packing of the molecule with the help of regular hydrogen bond and C-H···O interactions resulted in the formation of porous framework showing channels with pore size 7 A?.

Folding control of a non-natural glycopeptide using saccharide-coded structural information for polypeptides

We synthesized "glyco-arylopeptides", whose folding structure significantly changes depending on the kind of saccharide in their side chain. The saccharide moiety interacts with the main chain via hydrogen bonding, and the non-natural polypeptides form two well-defined architectures - (P)-31- and (M)-41-helices - depending on the length of the saccharide chains and even the configuration of a single stereo-genic center in the epimers.

THE SELECTIVE BOND CLEAVAGE OF ALDOHEXOSES BY THE IRON(III) CHLORIDE-CATALYZED PHOTOREACTION

Photoreaction of D-glucose, D-mannose, and D-galactose in pyridine in the presence of iron(III) chloride induced a selective bond cleavage at C1-C2 position, and produced corresponding 4-O-formyl-D-aldopentopyranoses.

Controlled site-selective glycosylation of proteins by a combined site- directed mutagenesis and chemical modification approach

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Task-oriented use of ionic liquids: Efficient acetylation of alcohols and phenols

The ionic liquid 1-butyl-3-methylimidazolium acetate proves to be an excellent reaction medium for the acetylation of alcohols and phenols, providing better conditions than the acidic 1-butyl-3-methylimidazolium bisulfate. Reactions were carried at room temperature, with only a 10% excess of acylating agent and with no other solvent or catalyst added.

Surface functionalization of nanomaterials with dendritic groups: Toward enhanced binding to biological targets

A diverse array of nanomaterials ranging from polymer assemblies to nanoparticles has been under development for biomedical applications in recent years. A key aspect of these applications is the ability to target the materials to the desired locations in vivo by exploiting their size or through the conjugation of active targeting groups. While nanoscale scaffolds may provide advantages such as the multivalent presentation of targeting ligands, the binding of these ligands may also be inhibited by interfering polymer chains at their surfaces. This aspect was investigated here by preparing poly(butadiene-block-ethylene oxide) vesicles and dextran-coated iron oxide nanoparticles functionalized with dendritic and nondendritic displays of mannose, a well-known multivalent ligand. The binding of these systems to the mannose-binding protein Concanavalin A was compared using a hemagglutination assay. It was found that the dendritic systems exhibited 1-2 orders of magnitude enhancement in binding affinity relative to the nondendritic displays. This result is attributed to the ability of the dendritic groups to overcome steric inhibition by polymer chains at the material surface and also to the presentation of ligands in localized clusters. It is anticipated that these results should be applicable to a wide range of nanomaterials with polymers at their surfaces and that the method by which biological ligands are conjugated to the surfaces of nanoparticles and polymer assemblies should be carefully considered.

An Oxygen-Tolerant PET-RAFT Polymerization for Screening Structure–Activity Relationships

The complexity of polymer–protein interactions makes rational design of the best polymer architecture for any given biointerface extremely challenging, and the high throughput synthesis and screening of polymers has emerged as an attractive alternative. A porphyrin-catalysed photoinduced electron/energy transfer–reversible addition-fragmentation chain-transfer (PET-RAFT) polymerisation was adapted to enable high throughput synthesis of complex polymer architectures in dimethyl sulfoxide (DMSO) on low-volume well plates in the presence of air. The polymerisation system shows remarkable oxygen tolerance, and excellent control of functional 3- and 4-arm star polymers. We then apply this method to investigate the effect of polymer structure on protein binding, in this case to the lectin concanavalin A (ConA). Such an approach could be applied to screen the structure–activity relationships for any number of polymer–protein interactions.

Selective binding of mannose-encapsulated gold nanoparticles to type 1 pili in Escherichia coli

The synthesis, characterization and biological application of mannose encapsulated gold nanoparticles (m-AuNP) are reported. m-AuNP is well dispersed and very stable without aggregation in the media of broad ion strength and pH ranges. The selective binding of m-AuNP to the mannose adhesin FimH of bacterial type 1 pili is demonstrated using transmission electron microscopy. The competition assay with free mannose suggests that m-AuNP binds FimH better than free mannose does. This work demonstrates that carbohydrate attached nanoparticles can be used as an efficient affinity label and a multi-ligand carrier in a biological system. Copyright

Formation of homooligosaccharides using base-promoted glycosylation of unprotected glycosyl fluorides

Homooligomeric saccharides are of general interest with potential applications in chemical, pharmaceutical, and food industry as well as for materials with novel properties. This contribution describes a methodology of a base-promoted "single step self-oligomerization" of glycosyl fluorides as donors leading to oligomers with up to ～25 saccharide units. The influences of base and reaction time were examined. Linkage analysis of the corresponding alditol acetates by GC/MS allowed for calculation of average structural elements of oligomers.

Synthesis of α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4- methylumbelliferone, a fluorogenic substrate for endo-α-1,2-mannosidase

α-D-Glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4- methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-α-1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-β-D-mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethane-sulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated α-D-glucopyranosyl-(1-3)-α-D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as a substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the α-glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 μg and with time up to 2 h. Vmax and Km were determined to be 0.17 nmol/mg × h and 3.7 mM, respectively.

Facile Preparation of per acetates and Per-3-bromobenzoates of α-Mono- And Disaccharides http://www.mdpi.org

A simple and convenient method for the preparation of fully acetylated and (3-bromo)benzoylated α-monosaccharides and disaccharides through vigorous mechanical mixing of solid reactants on a high speed shaker is described. Using this technique a variety o

Tumor microenvironment responsive supramolecular glyco-nanovesicles based on diselenium-bridged pillar[5]arene dimer for targeted chemotherapy

Supramolecular glyco-nanovesicles (SeSe-(P5)2?Man-NH3+) based on the host-guest complex of a diselenium-bridged pillar[5]arene dimer and a mannose derivative have been successfully developed for the first time, which possessed tumor microenvironment-respo

Silver Oxide Mediated Monotosylation of Poly(ethylene glycol) (PEG): Heterobifunctional PEG via Polymer Desymmetrization

Heterobifunctional poly(ethylene glycol)s (PEGs) are key structures for bioconjugation in the context of the PEGylation strategy to enhance blood circulation times of, for example, peptide drugs or stealth liposomes. The formation of heterobifunctional PEGs from symmetric PEG diols is challenging because of limited yields of the targeted monofunctional product and difficulties associated with separation steps. On the basis of a detailed comparison of reaction conditions, we have investigated a polymer desymmetrization strategy to maximize the yields of monofunctional PEG tosylate. The tosylation reaction in the presence of the heterogeneous catalyst silver oxide and potassium iodide in a specific stoichiometric ratio proved to be highly efficient, resulting in 71-76% yield of monofunctional PEG depending on molecular weight, exceeding the expected value of 50% in a statistical reaction without addition of a catalyst. For characterization as well as for the preparative separation of monotosylated PEG, we developed a HPLC method, using an evaporative light scattering detector, enabling both analytical and semipreparative separation of monotosylated PEGs on gram scale up to 20 000 g mol-1. To demonstrate the efficiency of the procedure, an α-azido-ω-methacryloyl-PEG was prepared as a building block suitable for azide-alkyne click-type reactions that can be incorporated into polymer networks via radical polymerization. We click-functionalized α-azido-ω-methacryloyl-PEG with a mannose-functionalized alkyne to enable functionalization of nanogels for enhanced cellular uptake via the mannose receptor. The synthesis strategy is suitable for a broad range of applications in the field of PEGylation and for hydrogel and nanogel functionalization.

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Manipulation of free carbohydrates via stannylene acetals. Preparation of β-per-O-acyl derivatives of D-mannose, L-rhamnose, 6-O-trityl-D-talose, and D-lyxose

A simple and high-yielding method for the preparation of 1-O-β-acyl derivatives of carbohydrates with an axial OH group at C-2 is described. It utilizes the property of unprotected carbohydrates to preferentially form 1,2-O-cis stannylene acetals, when tr

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A renewable, chemoselective, and quantitative ligand density microarray for the study of biospecific interactions

Novel renewable microarray technology has been developed to immobilize and release carbohydrates and proteins from self-assembled monolayers (SAMs) of electroactive quinone-terminated alkanethiolates on gold surfaces. This method may be applied to a variety of research fields for use in biosensor technology and the generation of renewable and tailored microarrays for biospecific cell-based assays.

Novel lipoamino acid- and liposaccharide-based system for peptide delivery: Application for oral administration of tumor-selective somatostatin analogues

Lipoamino acid and liposaccharide conjugates of somatostatin analogue TT-232 were synthesized to modify the physicochemical properties of the parent peptide. The relative position, the number, and the nature of the lipid and/or saccharide moieties were varied. Experiments in vitro clearly showed that many compounds modified at the N- and/or C-terminus with lipid or sugar moieties retained the biological activity of the parent compound. An interesting construct was synthesized containing lipid and sugar units at opposite ends of the somatostatin analogue, so that the entire molecule could be considered as an amphipathic surfactant.

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Glycosylated platinum(IV) prodrugs demonstrated significant therapeutic efficacy in cancer cells and minimized side-effects

Conjugates (A1-A5) of the Pt(iv) derivative (A6) with amino groups from peracetyl glucose, rhamnose and mannose with a propyl amino or ethyl amino linker at the reducing end were synthesized and exhibited significant therapeutic efficacy in tumour cells, especially for prostate cancer (PCa). The antitumor activities are greatly affected by glycosyl groups. Cytotoxic experiments in vitro indicated that the antitumor activities were increased by 5-fold when its Pt(iv) derivative was conjugated to S18 (IC50 = 4.82 ± 0.45 μM) and by 12-fold when conjugated to S21 (IC50 = 1.9 ± 0.67 μM). The mannose substituted Pt(iv) complexes A4 and A5 were also over an order of magnitude more potent towards HeLa, A549, MCF-7 and PC3 than cisplatin and oxaliplatin. Importantly, the glycosylated Pt(iv) derivatives A4 and A5 displayed potential safety for clinical therapeutic exposure with IC50 of 84 μM and 169 μM compared with cisplatin (IC50 = 8 μM) to 3T3. Cellular uptake and DNA platination are higher than cisplatin and oxaliplatin. ESI-MS analysis of A5 binding to 5′-dGMP revealed that bifunctional DNA lesions were formed. The antitumor activities in vivo showed that the MTD and LD50 for A4 and A5 are nearly 4-fold higher than that of oxaliplatin indicating the potential safety for the glycosylated Pt(iv) complexes.

Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection

Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.

Synthesis and biological activities of galactose–aspirin conjugate prodrug designed for ADEPT and PMT

Aspirin was used as the lead compound, and its structure was modified by galactosylation. Galactose-based aspirin prodrug was synthesized by using the α-d-glactopyranosyl bromide as glycosyl donor and aspirin as acceptor. The experimental method is simple and reproducible, has high yield and great practical value. The galactosylated aspirin prodrug was found to possess reduced cytotoxicity compared to aspirin, and selectively exhibited antiproliferative activity in the presence or in the absence of β-d-galactoside galactohydrolase with the approach of antibody-directed enzyme prodrug therapy (ADEPT) or the prodrug monotherapy (PMT).

Nonenzymatic synthesis of anomerically pure, mannosylbased molecular probes for scramblase identification studies

The chemical synthesis of molecular probes to identify and study membrane proteins involved in the biological pathway of protein glycosylation is described. Two short-chain glycolipid analogs that mimic the naturally occurring substrate mannosyl phosphoryl dolichol exhibit either photoreactive and clickable properties or allow the use of a fluorescence readout. Both probes consist of a hydrophilic mannose headgroup that is linked to a citronellol derivative via a phosphodiester bridge. Moreover, a novel phosphoramidite chemistry-based method offers a straightforward approach for the non-enzymatic incorporation of the saccharide moiety in an anomerically pure form.

Fe2(SO4)3·xH2O-catalyzed per-O-acetylation of sugars compatible with acid-labile protecting groups adopted in carbohydrate chemistry

Fully acetylated saccharides are inexpensive and very useful starting materials for the synthesis of many naturally occurring glycosides, oligosaccharides, and glycoconjugates. Ferric sulfate hydrate (Fe2(SO4)3·xH2O) was found to be a valuable Lewis acid promoter in the per-O-acetylation reaction of saccharides with acetic anhydride in 100% of conversion rate and 88-99% yields. Interestingly, the procedure is perfectly compatible with the presence of a variety of acid-labile protecting groups, such as isopropylidene, benzylidene, trityl, and TBDMS groups. The reactions were simply performed by stirring the mixture of a sugar with a slight excessive acetic anhydride in the presence of 2.0 mol % of Fe2(SO4)3·xH2O at rt and the pure products were obtained by a simple dilution of the reaction mixture with dichloromethane and washings with aqueous Na2CO3.

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

Selectivity of 1-O-Propargyl-D-Mannose Preparations

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

Isolation and characterization of triterpenoid saponins from leaves of Aralia nudicaulis L

Three new oleanolic glycosides (1–3), along with seven known saponins from various plants (4–10) were isolated for the first time from the leaves of Aralia nudicaulis. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, and HRESIMS. Nudicauloside A and B (1–2) have shown moderate anti-inflammatory activity, as demonstrated by inhibition of LPS-induced NO production in raw 264.7 murine macrophages (IC50 = 74–101 μM).