114297-26-6Relevant articles and documents
Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34
Ahadi, Somayeh,Awan, Shahid I.,Werz, Daniel B.
supporting information, (2020/05/04)
A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.
LANGERIN+ CELL TARGETING
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Paragraph 0375, (2019/08/08)
The present invention relates to the use of a vehicle for specific molecular targeting of Langerin+ cells, wherein the vehicle is capable of specifically binding to a Langerin+ cell, said vehicle comprising (a) at least one carrier and (b) at least one sa
Method for preparing 2-deoxy-D-glucose
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Paragraph 0024-0027, (2017/08/28)
The invention discloses a method for preparing 2-deoxy-D-glucose. According to the method, D-glucosamine which is low in price and easy to obtain serves as a starting material, p-anisaldehyde is used for protecting amino, pyridine serves as a solvent unde
Chemical Synthesis of Modified Hyaluronic Acid Disaccharides
Mende, Marco,Nieger, Martin,Br?se, Stefan
supporting information, p. 12283 - 12296 (2017/09/14)
Herein we report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d-glucose and d-glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C-6 of the β-d-glucuronic acid moiety with a view to structure-related biological activity tests. The orthogonal protecting group pattern allows ready access to the corresponding higher oligomers. Also, 1H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment.
Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors
Biswas, Nripendra N.,Yu, Tsz Tin,Kimyon, ?nder,Nizalapur, Shashidhar,Gardner, Christopher R.,Manefield, Mike,Griffith, Renate,Black, David StC.,Kumar, Naresh
, p. 1183 - 1194 (2017/02/18)
Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N′-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2?mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein.
Synthesis and characterisation of glucosamine-NSAID bioconjugates
Jones, Rachel A.,Thillier, Yann,Panda, Siva S.,Rivera Rosario, Nicole,Hall, C. Dennis,Katritzky, Alan R.
, p. 8325 - 8335 (2015/01/08)
Strategies to couple non-steroidal anti-inflammatory drugs (NSAIDs) to a glucosamine hydrochloride salt via an amino acid linker are investigated and a series of novel NSAID-glucosamine bioconjugates have been prepared. This journal is
MAGNETIC LABELING OF BACTERIA
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Page/Page column 60; 61, (2014/01/08)
The present invention provides novel methods of magnetically labeling a bacterial cell by contacting the call with an affinity ligand and subsequently contacting the cell with a magnetic agent, where the affinity ligand and magnetic agent include bioorthogonally reactive groups that can react with each other to form a covalent bond. Compounds, compositions, kits and applications of the method are also described.
DETECTION OF MYCOBACTERIA
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Page/Page column 51-52, (2011/04/18)
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 and antimicrobial activity of novel 3-benzyloxy-4-substituted-2- azetidinones: Formation of a hydrophobic layer via a self-organization effect
Hassan, Hammed H. A. M.,Soliman, Raafat
scheme or table, p. 1932 - 1947 (2011/10/09)
We report the synthesis of new persulfide-spacer N-substituted-2- azetidinone-D-glucosamine in an attempt to potentially provide new antibiotics. The Schiff base ligands considered for this study were derived from D-glucosamine and 2-hydroxybenzaldehyde, 4-methoxy-benzaldehyde, cinnamaldehyde, 4-chlorobenzaldehyde, and 4-hydroxy-3-methoxy-benzaldehyde. Staudinger [2+2] cycloaddition of benzyloxyacetyl chloride to the newly reported per-O-allyl-N-substituted benzylidene-2-deoxy - D-glucosamine provided the sugar-based monocyclic -lactams in moderate yields. Radical addition of 2-mercaptoethanol catalyzed by azobisisobutyronitrile to the per-O-allyl-N-substituted-2-azetidinone-D-glucosamine led to the corresponding persulfide-spacers in good yields. All new compounds were characterized by spectroscopic and spectrometric methods. The scanning electron microscopy image of 1,3,4,6-tetra-O-[3-(hydroxythioethyl)-propyl]-2-deoxy-2-N-[(3-benzyloxy-4-(4- chloropenyl)-2-azetidinone] - D-glucopyranoside, as a representative example, demonstrated a super hydrophobic layer formed via highly organized thioether spacers on gold as the adsorbate system through the formation of sulfur-gold bonds. The reported glucosides showed a moderate antifungal activity against Candida albicans while being slightly to moderately active against gram-positive and gram-negative bacteria used in this investigation at a concentration of 1 mg/mL dissolved in dimethyl sulfoxide. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Taylor & Francis Group, LLC.
Schiff bases from d-glucosamine and aliphatic ketones
Perez, Esther M.S.,Avalos, Martin,Babiano, Reyes,Cintas, Pedro,Light, Mark E.,Jimenez, Jose L.,Palacios, Juan C.,Sancho, Ana
scheme or table, p. 23 - 32 (2011/03/19)
Despite the comprehensive literature and enormous versatility of chiral imines derived from aminosugars and aldehydes, the corresponding counterparts generated from ketones remain an underestimated research subject. Filling in the gap, this manuscript she
