128188-35-2

Upstream product

• 128188-34-1 2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-trityl-β,β-trehalose 
• 64-19-7 acetic acid 
• 128188-34-1 2,3,4,2',3',4'-hexa-(benzyloxy)-6,6'-di-(trityloxy)-α,α-trehalose 
• 149113-51-9 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 
• 99-20-7 TREHALOSE 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1456898-33-1 2,3,4,2',3'-penta-O-benzyl-4',6'-O-benzylidene-α,α-D-trehalose 
• 100-39-0 benzyl bromide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 18929-82-3 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 

Downstream Products

• 89401-23-0 2,3,4,2',3',4'-hexa-(benzyloxy)-6-acetyloxy-α,α-trehalose 
• 81105-71-7 2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-p-tolylsulfonyl-α,α-trehalose 
• 89401-24-1 2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose 
• 89421-64-7 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose 
• 89401-25-2 2,3,4,2',3',4'-hexa-O-benzyl-6-O-corynomycoloyl-α-α-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.

Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry

Diphosphatidyltrehalose (diPT) is an immunogenic glycolipid, recently isolated from Salmonella Typhi. Despite rigorous structure elucidation, the sn-position of the acyl chains on the glycerol backbone had not been unequivocally established. A stereoselective synthesis of diPT and its regioisomer is reported herein. Using a hybrid MS3 approach combining collisional dissociation and ultraviolet photodissociation mass spectrometry for analysis of the regioisomers and natural diPT, the regiochemistry of the acyl chains of this abundant immunostimulatory glycolipid was established.

The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle

We demonstrate that the natural product brartemicin, a newly discovered inhibitor of cancer cell invasion, is a high-affinity ligand of the carbohydrate-recognition domain (CRD) of the C-type lectin mincle. Recent studies have revealed that mincle is a ke

Synthesis and structure - Activity relationships studies of brartemicin analogs as anti-invasive agents

Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to find more potent anti-invasive agents and study the structure-activity relationships, a series of 19 brartemicin analogs we

Self-assembling properties of 6-O-alkyltrehaloses under aqueous conditions

In this study, we report the self-assembling properties of 6-O-alkyltrehaloses with different chain lengths, that is, octyl, decyl, dodecyl, tetradecyl, and hexadecyl, under aqueous conditions. The materials were synthesized from trehalose via five reacti

Self-assembling property of 6,6'-Di-O-octyltrehalose under aqueous conditions

In this study, we synthesized a new trehalose-based amphiphile, 6,6'-di-O-octyltrehalose, from trehalose by five reaction steps. The SEM and TEM images of the sample prepared by drying its aqueous dispersion showed the formation of morphologically control

Synthesis and evaluation of trehalose-based compounds as anti-invasive agents

Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to explore the preliminary structure-activity relationship and obtain more potent inhibitors, a series of brartemicin analogs

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.

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.