95580-90-8

Usage

Chemical structure

The compound is an azide derivative of the sugar rhamnose, with acetyl groups attached to the 2, 3, and 4 positions of the sugar ring.

Source

Rhamnose is a naturally occurring sugar found in various plants and bacteria.

Uses

The compound is commonly used in chemical synthesis and organic chemistry research, as a reagent in the synthesis of various rhamnose derivatives and glycoconjugates, and in the study of carbohydrate biochemistry.

Importance

It is important for the development of new pharmaceuticals and biomaterials, and for the development of new carbohydrate-based compounds for various applications.

Selectivity

2,3,4-Tri-O-acetyl-α-L-rhamnopyranosyl azide is known for its ability to selectively modify carbohydrates, making it a valuable tool in the development of new carbohydrate-based compounds.

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 73-34-7 L-rhamnose 
• 108-24-7 acetic anhydride 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 69980-52-5 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 
• 28915-80-2 2,3,4-tri-O-acetyl-L-rhamnopyranose 
• 141607-27-4 diphenyl (tri-O-acetyl-β-L-rhamnopyranosyl) phosphate 

Relevant academic research and scientific papers

Synthesis of rhamnosylated arginine glycopeptides and determination of the glycosidic linkage in bacterial elongation factor P

A new class of N-linked protein glycosylation-arginine rhamnosylation-has recently been discovered as a critical modification for the function of bacterial elongation factor P (EF-P). Herein, we describe the synthesis of suitably protected α- and β-rhamnosylated arginine amino acid “cassettes” that can be directly installed into rhamnosylated peptides. Preparation of a proteolytic fragment of Pseudomonas aeruginosa EF-P bearing both α- and β-rhamnosylated arginine enabled the unequivocal determination of the native glycosidic linkage to be α through 2D NMR and nano-UHPLC-tandem mass spectrometry studies.

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Novel carbohydrate modified berberine derivatives: Synthesis and: In vitro anti-diabetic investigation

Berberine is a bioactive alkaloid used in Chinese medicine and has numerous positive effects on biological systems. This paper describes the facile and highly efficient synthesis of some carbohydrate modified berberine derivatives, and conjugation of the carbohydrate moiety with berberine was finished by "click" chemistry. The cytotoxicity and anti-diabetic measurements of all berberine derivatives were accomplished on HepG2 cell lines, and the results indicated that most of the derivatives exhibit higher anti-diabetic activity than berberine. The mannose modified berberine derivative has significantly lower cytotoxicity than berberine, and the induced IC50 value of this derivative is nearly 1.5 times that of berberine. Furthermore, this mannose modified berberine derivative exhibits high anti-diabetic activity at both high and low drug concentrations, thereby indicating its potential application for the development of novel anti-diabetic drugs.

Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity

The development of entry inhibitors is an emerging approach to the inhibition of influenza virus. In our previous research, oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor. Herein, as a further study, we report the preparation of a series of OA-saccharide conjugates via the CuAAC reaction, and the anti-influenza activity of these compounds was evaluated in vitro. Among them, compound 11b, an OA-glucose conjugate, showed a significantly increased anti-influenza activity with an IC50 of 5.47 μM, and no obvious cytotoxic effect on MDCK cells was observed at 100 μM. Hemagglutination inhibition assay and docking experiment indicated that 11b might interfere with influenza virus infection by acting on HA protein. Broad-spectrum anti-influenza experiments showed 11b to be robustly potent against 5 different strains, including influenza A and B viruses, with IC50 values at the low-micromole level. Overall, this finding further extends the utility of OA-saccharide conjugates in anti-influenza virus drug design.

Synthesis of biurets: Via TMSNCO addition to 1-aminosugars: Application in the de novo synthesis of dC oxidation products

The reaction between 1-aminosugars and trimethylisocyanate (TMSNCO) was optimised as a one-step synthetic strategy for the synthesis of sugar biurets. This protocol was successfully applied to a number of 1-aminosugars, which exclusively provided the corresponding biurets in 67-99% yields. The new methodology was applied in the de novo synthesis of N1-(2-deoxy-α/β-d-erythro-pentofuranosyl)biuret (dfBU) and N1-(2-deoxy-α/β-d-erythro-pentopyranosyl)biuret (dpBU), two known DNA lesions arising from the hydroxyl radical induced decomposition of 2′-deoxycytidine (dCyd).

Synthesis and Antifungal Activities of Glycosylated Derivatives of the Cyclic Peptide Fungicide Caspofungin

Diseases caused by systemic fungal infections have become a significant clinical problem in recent decades. A series of glycosyl derivatives of the approved cyclic peptide antifungal drug caspofungin conjugated with β-D-glucopyranose, β-D-galactopyranose, β-D-xylopyranose, β-L-rhamnopyranose, β-maltose and β-lactose units were designed, synthesized, and evaluated as new potential antifungal drugs. The compounds were obtained by coupling the corresponding glycosyl amines to the free primary amino groups of caspofungin through a bifunctional glutaryl linker. In contrast to caspofungin, these glycosylated derivatives are soluble in water, but are not hygroscopic and moreover, are more stable than caspofungin under high humidity and temperature. CD studies showed that glycosylation has very little impact on the conformation of the cyclic peptide of caspofungin. Invitro antifungal tests against seven human pathogenic fungi revealed that the caspofungin-monosaccharide conjugates, but not the disaccharide conjugates, have increased antifungal activities against the majority of tested fungus species relative to caspofungin. The β-D-glucopyranosyl derivative 2a showed the strongest and broadest antifungal activity, providing a lead for further studies.

A generalized procedure for the one-pot preparation of glycosyl azides and thioglycosides directly from unprotected reducing sugars under phase-transfer reaction conditions

Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding procedure for the preparation of 1,2-trans-glycosyl azides and thioglycosides. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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.

APPLICATION OF PHENYL 1-SELENOGLYCOSIDES IN THE SYNTHESIS OF A CELL-WALL TETRAMERIC FRAGMENT OF PROTEUS VULGARIS STRAIN 5/43

DAST-assisted rearrangement of 3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl azide followed by treatment of the generated fluorides with ethanethiol and BF3*OEt2 gave glycosyl donor ethyl 3-O-allyl-2-azido-4-O-benzyl-2,6-dideoxy-1-thio-α/β-L-glucopyranoside.St

Process for the preparation of glycosyl azides

A process for stereospecific preparation of glycosyl azides by reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent is disclosed.