103128-35-4

Upstream product

• 100-39-0 benzyl bromide 
• 116594-37-7 4,6-O-benzylidene-2,3,2’,3’4’,6’-hexa-O-benzyl-α,α’-trehalose 
• 1498304-92-9 6-O-diphenoxyphosphoryl-2,3,4,2’,3’,4’,6’-hepta-O-benzyl-α,α’-trehalose 
• 99-20-7 TREHALOSE 
• 1253692-53-3 6-O-tert-butyldiphenylsilyl-2,3,4,2',3',4',6'-hepta-O-benzyl-α,α-D-trehalose 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 100-44-7 benzyl chloride 
• 58781-26-3 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-(1?1)-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 

Downstream Products

• 1274878-22-6 6-O-hexanoyl-2,3,4,2',3',4,6'-hepta-O-benzyl-α,α-D-trehalose 
• 1352302-95-4 2,3,4,2',3',4',6'-hepta-O-benzyl-6-O-trifluoromethanesulfonyl-α,α-D-trehalose 
• 1352302-92-1 2,3,4,2',3',4',6'-hepta-O-benzyl-6-O-(2-bromoacetyl)-α,α-D-trehalose 
• 827026-15-3 (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide 
• 827026-12-0 6-azido-2,2',3,3',4,4',6'-hepta-O-benzyl-6-deoxy-α,α'-trehalose 
• 827026-14-2 (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester 
• 827026-13-1 6'-azido-2,2',3,3',4,4'-hexa-O-benzyl-6'-deoxy-α-D-trehalose 
• 1328912-17-9 6-O-(hexylphosphorylfluoro)-2,3,4,2',3',4,6'-hepta-O-benzyl-α,α-D-trehalose 
• 1328912-14-6 6-O-(hexylphosphoryl)-2,3,4,2',3',4,6'-hepta-O-benzyl-α,α-D-trehalose 

Relevant academic research and scientific papers

Rational design of first generation inhibitors for trehalose 6-phosphate phosphatases

In this study, trehalose 6-phosphate phosphatase (T6PP) was targeted for inhibitor development. T6PP catalyzes the hydrolysis of trehalose-6-phosphate to form trehalose and inorganic phosphate, a reaction essential to important fungal, bacterial, and nematodal pathogens. At the current time, there are no specific inhibitors of T6PP available to serve as tools for interrogating its structure and function nor as leads for pharmaceutical applications. Herein, we describe the synthesis of non-hydrolysable mimics of trehalose-6-phosphate, which incorporate 6-sulfate (1), -phosphonate (2), -fluorophosphonate (3) and –boronate (4) groups in place of the 6-phosphate moiety of the substrate. The inhibitory efficacies of these adducts were evaluated against trehalose 6-phosphate phosphatases selected from evolutionarily distant pathogenic bacteria and nematodes. Phosphonates 2 and 3 were found to display good inhibitory activities against the T6PPs, while the sulfate analog, trehalose-6-sulfate, proved to be a particularly effective broad-spectrum inhibitor of these phosphatases and an ideal prototype for optimization.

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.

Simple one-pot regioselective 6-O-phosphorylation of carbohydrates and trehalose desymmetrization

Biologically essential carbohydrate 6-phosphates, especially trehalose 6-phosphate, can be synthesized easily in excellent overall yields in 2 steps involving minimum protecting group manipulations. We can cleave the diphenylphosphate group for further synthetic objectives.

Covalent linkage of N-methyl-6-oxyquinolinium betaine to trehalose

The common route to link quinolinium and pyridinium fluorophores to biomolecules via bromoacetic acid has failed in labeling the disaccharide trehalose with N-methyl-6-oxyquinolinium betaine: the unexpected, extremely high instability of the N-carboxymeth

ESI-MS assay of M. tuberculosis cell wall antigen 85 enzymes permits substrate profiling and design of a mechanism-based inhibitor

Mycobacterium tuberculosis Antigen 85 enzymes are vital to the integrity of the highly impermeable cell envelope and are potential therapeutic targets. Kinetic analysis using a label-free assay revealed both mechanistic details and a substrate profile tha

DETECTION OF MYCOBACTERIA

A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

Synthesis of trehalose-based compounds and their inhibitory activities against Mycobacterium smegmatis

The synthesis of a library of trehalose-based compounds has been accomplished, and their activities against Mycobacterium smegmatis have been determined. A preliminary structure-activity relationship (SAR) is reported. Despite not having a potent lead, on

α-D-glucosylation by 6-O-Acetyl-2,3,4-tri-O-benzyl-D-glucopyranose Using Trimethylsilyl Triflate and Pyridine. Synthesis of α-Maltosyl and α-isomaltosyl α-D-Glucosides

The D-glucosylation of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside and methyl 2,3,6-tri-O-benzyl-β-D-glucupyranoside by 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose using pyridine and excess trimethylsilyl triflate was carried out in dichloromethane, 1,2 dimethoxyethane, and acetonitrile.In a given solvent, the selectivity of the reaction varied depending on the type of hydroxyl group of the glucosyl acceptors.The D-glucosylation of these acceptors with 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose employing this reagent system in dichloromethane proceeded with good α-selectivity irrespective of the type of the hydroxyl group.This α-D-glucosylation was applied for the synthesis of O-α-D-glucopyranosyl-(1->4)- and -(1->6)-α-D-glucopyranosyl α-D-glucopyranosides from α,α-trehalose.