18929-82-3

Upstream product

• 32849-07-3 4,6:4',6'-di-O-benzylidene-α,α-trehalose 2,2'-ditosylate 
• 585-91-1 neotrehalose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 99-20-7 TREHALOSE 
• 100-52-7 benzaldehyde 

Downstream Products

• 89421-66-9 4,6:4',6'-di-O-benzylidene-2-O-(trifluoromethylsulfonyl)-α,α-trehalose 
• 89387-65-5 4,6:4',6'-di-O-benzylidene-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose 
• 91667-48-0 ammonium 4,6:4',6'-di-O-benzylidene-α,α-trehalose 2-sulfate 
• 91667-47-9 ammonium 4,6:4',6'-di-O-benzylidene-α,α-trehalose 3-sulfate 
• 129727-78-2 4,6-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranosyl 4,6-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside 
• 82305-37-1 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 33072-96-7 4,6:4,'6'-di-O-benzylidene-α,α-trehalose 2,3,2',3'-tetratosylate 
• 32849-13-1 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranosyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 32849-09-5 4,6:4'6'-di-O-benzylidene-α,α-trehalose 2-tosylate 
• 32849-07-3 4,6:4',6'-di-O-benzylidene-α,α-trehalose 2,2'-ditosylate 
• 32849-10-8 4,6:4,'6'-di-O-benzylidene-α,α-trehalose 2,3,2'-tritosylate 
• 161754-76-3 2,3,2',3'-tetra-O-acetyl 4,6:4',6'-di-O-benzylidene-α,α'-trehalose 
• 61216-76-0 2,2'-di-O-benzoyl-4,6:4',6'-di-O-benzylidene-α,α-D-trehalose 
• 67693-36-1 2,3,2',3'-tetra-O-benzyl-4,6-O-benzylidene-α,α-D-trehalose 

Relevant academic research and scientific papers

Synthesis, trehalase hydrolytic resistance and inhibition properties of 4- and 6-substituted trehalose derivatives

Although trehalose has recently gained interest because of its pharmaceutical potential, its clinical use is hampered due to its low bioavailability. Hence, hydrolysis-resistant trehalose analogues retaining biological activity could be of interest. In this study, 34 4- and 6-O-substituted trehalose derivatives were synthesised using an ether- or carbamate-type linkage. Their hydrolysis susceptibility and inhibitory properties were determined against two trehalases, i.e. porcine kidney and Mycobacterium smegmatis. With the exception of three weakly hydrolysable 6-O-alkyl derivatives, the compounds generally showed to be completely resistant. Moreover, a number of derivatives was shown to be an inhibitor of one or both of these trehalases. For the strongest inhibitors of porcine kidney trehalase IC50 values of around 10 mM could be determined, whereas several compounds displayed sub-mM IC50 against M. smegmatis trehalase. Dockings studies were performed to explain the observed influence of the substitution pattern on the inhibitory activity towards porcine kidney trehalase.

Novel trehalose-cored amphiphiles and uses thereof

The present invention relates to a newly-developed trehalose-based amphipathic compound, a producing method thereof, and a method of extracting, solubilizing, stabilizing, crystallizing, or analyzing membrane proteins using the same. In addition, compared

Trehalose-cored amphiphiles for membrane protein stabilization: Importance of the detergent micelle size in GPCR stability

Despite their importance in biology and medicinal chemistry, structural and functional studies of membrane proteins present major challenges. To study diverse membrane proteins, it is crucial to have the correct detergent to efficiently extract and stabilize the proteins from the native membranes for biochemical/biophysical downstream analyses. But many membrane proteins, particularly eukaryotic ones, are recalcitrant to stabilization and/or crystallization with currently available detergents and thus there are major efforts to develop novel detergents with enhanced properties. Here, a novel class of trehalose-cored amphiphiles are introduced, with multiple alkyl chains and carbohydrates projecting from the trehalose core unit are introduced. A few members displayed enhanced protein stabilization behavior compared to the benchmark conventional detergent, n-dodecyl-β-d-maltoside (DDM), for multiple tested membrane proteins: (i) a bacterial leucine transporter (LeuT), (ii) the R. capsulatus photosynthetic superassembly, and (iii) the human β2 adrenergic receptor (β2AR). Due to synthetic convenience and their favourable behaviors for a range of membrane proteins, these agents have potential for membrane protein research. In addition, the detergent property-efficacy relationship discussed here will guide future design of novel detergents.

Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals

Trehalose dibenzylidene and substituted dibenzylidene acetals were reductively opened either at O6 or O4 in a regioselective manner by using a DIBAL stock solution prepared in toluene or dichloromethane, respectively, to achieve desymmetrization of the trehalose core. The method was applied to synthesize various biologically important unsymmetrically substituted trehalose glycoconjugates, including a mycobacterial trisaccharide, a 4-epi-trehalosamine analog and a maradolipid.

STABILIZATION OF BIOMOLECULES USING SUGAR POLYMERS

Compositions and methods for stabilizing biomolecules are disclosed. Specifically, the compositions include novel homopolymers or copolymers containing trehalose side chains conjugated to biomolecules. When such homopolymers or copolymers are placed in cl

Synthesis and properties of dodecyl trehaloside detergents for membrane protein studies

Sugar-based detergents, mostly derived from maltose or glucose, prevail in the extraction, solubilization, stabilization, and crystallization of membrane proteins. Inspired by the broad use of trehalose for protecting biological macromolecules and lipid b

Synthesis of per- and poly-substituted trehalose derivatives: Studies of properties relevant to their use as excipients for controlled drug release

Per- and poly-substituted oligosaccharide derivatives, with trehalose cores, have been prepared and assessed for their potential for use as excipients in controlled-release formulations. The synthesized compounds, generally with acyl and amido substituent

SULFOGLYCOLIPID ANTIGENS, THEIR PROCESS OF PREPARATION, AND THEIR USE AGAINST TUBERCULOSIS

The present invention relates to compounds of the following general formula (I) their process of preparation and their use in the treatment or the prophylaxis of tuberculosis.

Synthesis of diacylated trehalose sulfates: Candidates for a tuberculosis vaccine

Able antigen analogues: Analogues of the mycobacterial sulfoglycolipid antigen 1 isolated from Mycobacterium tuberculosis have been prepared by a short and general route. Some derivatives showed interesting immunogenic properties and activated cytotoxic T

Sonochemistry: A powerful way of enhancing the efficiency of carbohydrate synthesis

Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation (acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.