6801-92-9

Upstream product

• 66854-07-7 dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside 
• 112-53-8 1-dodecyl alcohol 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 1427214-08-1 dodecyl 4,6-O-benzylidene-β-D-galactopyrnoside 
• 440652-81-3 isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 504422-48-4 dodecyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 258349-81-4 dodecyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-58-6 dodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 504422-53-1 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-52-0 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-50-8 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-54-2 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-51-9 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-57-5 dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-56-4 dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 263247-08-1 dodecyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside 
• 263247-10-5 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 263247-09-2 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside 

Relevant academic research and scientific papers

Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics

A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.

Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles

Surfactants are not only pivotal constituents in any biological organism in the form of phospholipids, they are also essential for numerous applications benefiting from a large, internal surface, such as in detergents, for emulsification purposes, phase transfer catalysis or even nanoparticle stabilization. A particularly interesting, green class of surfactants contains glycoside head groups. Considering the variability of glycosides, a large number of surfactant isomers become accessible. According to established models in surfactant science such as the packing parameter or the hydrophilic lipophilic balance (HLB), they do not differ from each other and should, thus, have similar properties. Here, we present the preparation of a systematic set of glycoside surfactants and in particular isomers. We investigate to which extent they differ in several key features such as critical aggregation concentration, thermodynamic parameters, etc. Analytical methods like isothermal titration calorimetry (ITC), tensiometry, dynamic light scattering (DLS), small angle-X-ray scattering (SAXS), transmission electron microscopy (TEM) and others were applied. It was found that glycosurfactant isomers vary in their emulsification properties by up to two orders of magnitude. Finally, we have investigated the role of the surfactants in a microemulsion-based technique for the generation of zinc oxide (ZnO) nanoparticles. We found that the choice of the carbohydrate head has a marked effect on the shape of the formed inorganic nanocrystals.

Novel mixed-heteroatom macrocycles via templating: A new protocol

A series of novel thiadiaza and triaza crown ether attached galactose- and glucose-based glycolipids is synthesized, applying a new strategy. The key step is the formation of α-chloroacetamido precursors (14 and 21) from selectively protected bis(cyanomethyl)-glycolipids (13 and 19) in two steps. The cyclization reaction furnishes good yields in relatively short times in aqueous ethanol or acetonitrile. To generalize this method, macrocycles 3 and 25 are reported as well. Attempts to use the traditional synthetic approaches for cyclization failed to provide reasonable yields.

The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure α- or β-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested.

Easy production of a glycolipid analogue using animal cells in culture

A glycolipid analogue, GM4-type ganglioside, was obtained by a combination of chemical synthesis and biosynthetic processes in animal cells with dodecyl β-d-galactoside (Gal C12) as primer. The primer was conveniently prepared in two steps: glycosylation, followed by deacetylation. The primer was introduced to mouse melanoma B16 cells to serve as substrate for cellular, enzyme-catalyzed glycosylation. Incubation of the cells in the presence of the primer resulted in sialylation of the galactose residue to afford a GM4 analogue that was released from the cells to the culture medium. The strategy of preparation of the GM4 analogue described in this study is a viable alternative to the existing methods. The saccharide-primer method is fast, convenient, not requiring expensive enzymes and glycosyl donors, and highly stereoselective.

Simple and convenient synthesis of a fluorinated GM4 analogue

A series of fluorinated galactosides, dodecyl 2-deoxy-2-fluoro-β-d-galactopyranoside (2F Gal), dodecyl 4-deoxy-4-fluoro-β-d-galactopyranoside (4F Gal) and dodecyl 6-deoxy-6-fluoro-β-d-galactopyranoside (6F Gal), was chemically synthesized and introduced to B16 cells to serve as scaffolds for cellular enzyme glycosylation. Results showed that the presence of fluorine exercised significant effects on cell viability. Among the fluorinated galactosides used, 2F Gal was glycosylated to afford a GM4 analogue.

Effect of anomeric linkage on the sialylation of glycosides by cells

The synthesis of sialylated glycosides using saccharide primers and cells was investigated. α·and β·Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of α- and β-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The β-dodecyl galactoside primer was sialylated but the α-dodecyl galactoside primer was not. Both the α- and β-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the α- or β-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is β-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur. Copyright Taylor & Francis, Inc.

Thermotropic and lyotropic properties of long chain alkyl glycopyranosides: Part III: pH-sensitive headgroups

As part of a series of papers, the influence of carbohydrate headgroups and aliphatic chains on the mesogenic properties of glycolipids was investigated. Alkyl glycosides with different types of aliphatic chains were synthesised. Neutral glycolipids were oxidized to their uronic acid derivatives, using the well established TEMPO-oxidation. For comparison a 6-deoxy-6-amino alkylglucopyranoside was synthesised. In addition, the thermotropic and lyotropic phase behaviour of the synthesised compounds were investigated. The thermotropism was characterised by polarising microscopy, the lyotropism by the contact preparation method.

Synthesis of C7-C16-alkyl glycosides: Part III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (galactose) with fatty alkanols is used in a synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.

Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside

For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.