30923-00-3

Upstream product

• 99-20-7 TREHALOSE 
• 23103-34-6 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranoside 
• 23089-74-9 2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-(4-toluenesulfonyl)-α,α'-trehalose 
• 18933-87-4 6,6'-diazido-2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-D-trehalose 
• 577969-86-9 2,3,2',3'-tetra-O-benzoyl-4,6:4',6'-di-O-benzylidene-α,α-trehalose 
• 18929-82-3 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 
• 18933-86-3 6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose 
• 42891-34-9 2,2',3,3',4,4'-hex-O-acetyl-6,6'-dideoxy-6,6'-dibromo-α,α-D-trehalose 
• 67398-72-5 2,2',3,3',4,4'-hexa-O-acetyl-α,α'-trehalose 
• 23089-73-8 2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-methylsulfonyl-α,α'-trehalose 
• 18933-88-5 6-azido-6-deoxy-α-D-glucopyranosyl-(1→1)-6-azido-6-deoxy-α-D-glucopyranoside 

Downstream Products

• 714963-90-3 {[((2R,3S,4S,5R,6R)-6-{(2R,3R,4S,5S,6R)-6-[(2-Benzyloxycarbonylamino-acetylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-methyl}-carbamic acid benzyl ester 
• 714963-89-0 {3-[((2R,3S,4S,5R,6R)-6-{(2R,3R,4S,5S,6R)-6-[(4-Benzyloxycarbonylamino-butyrylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-propyl}-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Trehalose diamide glycolipids augment antigen-specific antibody responses in a Mincle-dependent manner

Many studies have investigated how trehalose glycolipid structures can be modified to improve their Macrophage inducible C-type lectin (Mincle)-mediated adjuvanticity. However, in all instances, the ester-linkage of α,α?-trehalose to the lipid of choice remained. We investigated how changing this ester-linkage to an amide influences Mincle signalling and agonist activity and demonstrated that Mincle tolerates this functional group change. In in vivo vaccination studies in murine and ovine model systems, using OVA or Mannheimia haemolytica and Mycoplasma ovipneumoniae as vaccine antigens, respectively, it was demonstrated that a representative trehalose diamide glycolipid was able to enhance antibody-specific immune responses. Notably, IgG titres against M. ovipneumoniae were significantly greater when using trehalose dibehenamide (A-TDB) compared to trehalose dibehenate (TDB). This is particularly important as infection with M. ovipneumoniae predisposes sheep to pneumonia.

Synthesis, Conformational Flexibility and Preliminary Complexation Behaviour of α,α'-Trehalose-based Macrocycles Containing Thiourea Spacers

An efficient synthesis of macrocyclic ligands incorporating two α,α'-trehalose subunits linked through the primary C-6,6' positions by means of 1,3-thiourea spacers is reported; the Z/E configuration of the N-C(=S) bonds is governed by intramolecular hydrogen bonding as well as steric factors.

Amide-linked brartemicin glycolipids exhibit Mincle-mediated agonist activity in vitro

Lipidated derivatives of the natural product brartemicin show much promise as vaccine adjuvants due to their ability to signal through the Macrophage Inducible C-type Lectin (Mincle). We synthesised three lipophilic amide-linked brartemicin derivatives and compared their agonist activity to that of their ester-linked counterparts in vitro. We demonstrate that the brartemicin amide derivatives activate bone-marrow-derived macrophages (BMDMs) in a Mincle-dependent manner, as evidenced by the production of the pro-inflammatory cytokine IL-1β in wildtype but not Mincle-/- cells. The amide derivatives showed activity that was as good as, if not better than, their ester counterparts. Two of the amide derivatives, but none of the ester-derivatives, also led to the production of IL-1β by human-derived monocytes. As the production of IL-1β is a good indicator of vaccine adjuvanticity potential, these findings suggest that amide-linked brartemicin derivatives show particular promise as vaccine adjuvants.

Mono- And dialdehyde of trehalose: New synthons to prepare trehalose bio-conjugates

Trehalose, a non-reducing disaccharide of glucose, is a natural bioactive and non-toxic sugar. It is found in many organisms that synthesise it when their cells are exposed to stress conditions. While not produced by mammalian cells, this disaccharide and also some of its derivatives have been shown to have a number of interesting properties that indicate their importance in the treatment of certain human diseases. Differentiating the two glucosyl moieties in the trehalose molecule has often been a synthetic challenge. We report here an easy way to obtain the monoaldehyde of trehalose, as well as the relevant symmetrical dialdehyde. The reactivity of the aldehyde functionalities involved in the molecular structure of these synthons allows the easy preparation of the corresponding amino or carboxy derivatives of trehalose, as well the synthesis of some new trehalose conjugates useful for diagnostic or therapeutic purposes. This journal is

α,α-Trehalose derivatives bearing guanidino groups as inhibitors to HIV-1 Tat-TAR RNA interaction in human cells

Replication of HIV-1 requires specific interactions of Tat protein with TAR RNA. Disruption of Tat-TAR RNA interaction could inhibit HIV-1 replication. Here four target compounds were designed and synthesized to bind to TAR RNA for blocking the interaction of Tat-TAR RNA. The core molecule 6,6 ′-diamino-6,6′-dideoxy-α,α- trehalose was obtained from selective bromination of, α,α-trehalose at C-6,6′, followed by acetylation, azide displacement, deacetylation, and reduction. Coupling of the core molecule with the protected amino acid, then deprotection and guanidinylation generated the novel α,α-trehalose derivatives. Their abilities to inhibit Tat-TAR RNA interaction in human cells were determined by a Tat-dependent HIV-1 LTR-driven CAT assays.

Supramolecular structures of substituted α,α′-trehalose derivatives

The structures of five substituted α,α′-trehalose trehalose derivatives have been determined, and these are compared with those of four previously published analogues. In 2,2′,3,3′,4,4′- hexaacetato-6,6′-bis-O-methylsulfonyl-α,α′-trehalose, C26

Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis

Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6′-dideoxytrehalose, including N,N′-dialkylamino and 6,6′-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Ra and a panel of clinical isolates of Mycobacterium avium. 6,6′-Diaminotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines.

Gemini surfactants with a disaccharide spacer

A gemini surfactant is an amphiphile possessing (in sequence) the following: hydrocarbon tail/polar group/spacer/polar group/hydrocarbon tail. Widespread interest in geminis has emerged recently from both industrial and academic laboratories. In the prese