Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae

Susanto, Woen; Kong, Keng He; Hua, Kuo-Feng; Wu, Shih‐Hsiung; Lam, Yulin

doi:10.1016/j.tetlet.2018.12.031

Cited by 5 publications

(3 citation statements)

References 22 publications

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“…Intense efforts have been devoted for the introduction of a pyruvyl ketal to carbohydrates, including acid-catalyzed ketalation with pyruvate , or pyruvate dialkyl dithioketal, ,− and oxidative formation of a carboxyl moiety in a ketal precursor. − These methods have facilitated the syntheses of important bacterial glycans, including the capsular polysaccharide (CPS) of E. coli O101:K103:H – , the exopolysaccharide of Rhizobium leguminosarum K87, the cell wall glycolipid of Mycobacterium smegmatis, , the polysaccharide A1 of Bacteroides fragilis, − the CPS of Streptococcus pneumoniae serotypes 4 and 27, , the CPS of Klebsiella pneumoniae, and the secondary cell wall polysaccharide of Bacillus anthracis (Figure ). We indicated that the ( S )-2,3- O -pyruvate is a key motif for the immunological response to S.…”

Section: Introductionmentioning

confidence: 99%

Chemical Synthesis and Antigenicity Evaluation of Shigella dysenteriae Serotype 10 O-Antigen Tetrasaccharide Containing a (S)-4,6-O-Pyruvyl Ketal

Qin

Tian

et al. 2022

J. Am. Chem. Soc.

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Shigella is the second most common etiologic pathogen responsible for childhood acute diarrhea. An anti-Shigella vaccine is still eagerly awaited due to the increasing drug resistance of this pathogen. The Shigella O-antigen is a promising vaccine target. To identify the immune epitopes of the glycan, the first total synthesis of Shigella dysenteriae serotype 10 O-antigen tetrasaccharide containing a (S)-4,6-O-pyruvyl ketal was completed. The 1,2-trans-β-glycosylation & C2 epimerization and conformational locking strategies facilitated the construction of two 1,2-cis-β-glycosidic linkages. The reactivities of both the glycosyl donor and acceptor were improved by adding electron-donating benzyl groups, enabling an efficient assembly of the tetrasaccharide. The (S)-4,6-Opyruvyl ketal was introduced at the final stage due to its influence on the glycosylation stereospecificity and efficiency. In addition, (R)-4,6-O-pyruvylated and nonpyruvylated tetrasaccharides and three further fragments were synthesized. Glycan microarray screening revealed that the tetrasaccharide repeating unit is the key antigenic epitope of the O-antigen. Moreover, the (S)-4,6-O-pyruvyl ketal is an essential structural feature of this antigen for designing carbohydrate-based vaccines against S. dysenteriae serotype 10. The comparison of the (S)-4,6-O-pyruvylated glycan and its (R)-epimer will set an example for biological evaluation of other bacterial glycans containing pyruvyl ketals.

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Section: Introductionmentioning

confidence: 99%

Chemical Synthesis and Antigenicity Evaluation of Shigella dysenteriae Serotype 10 O-Antigen Tetrasaccharide Containing a (S)-4,6-O-Pyruvyl Ketal

Qin

Tian

et al. 2022

J. Am. Chem. Soc.

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“…The Enterobacteriaceae family is one of the most clinically prominent bacteria groups. One of the main gram-negative pathogen is Klebsiella pneumoniae ( K. pneumoniae ), which causes opportunistic infections, such as pneumonia, sepsis and inflammation of the urinary tract 1 . Another gram-negative that compose the entereobacteriaceae family is Escherichia coli , which are not typically pathogenic to humans and have the ability to cause several diseases in different sites including gastrointestinal tract, the renal system and the central nervous system 2 , 3 .…”

Section: Introductionmentioning

confidence: 99%

Identification of resistance in Escherichia coli and Klebsiella pneumoniae using excitation-emission matrix fluorescence spectroscopy and multivariate analysis

Costa

Bezerra

Neto

et al. 2020

Sci Rep

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Klebsiella pneumoniae and Escherichia coli are part of the Enterobacteriaceae family, being common sources of community and hospital infections and having high antimicrobial resistance. This resistance profile has become the main problem of public health infections. Determining whether a bacterium has resistance is critical to the correct treatment of the patient. Currently the method for determination of bacterial resistance used in laboratory routine is the antibiogram, whose time to obtain the results can vary from 1 to 3 days. An alternative method to perform this determination faster is excitation-emission matrix (EEM) fluorescence spectroscopy combined with multivariate classification methods. In this paper, Linear Discriminant Analysis (LDA), Quadratic Discriminant Analysis (QDA) and Support Vector Machines (SVM), coupled with dimensionality reduction and variable selection algorithms: Principal Component Analysis (PCA), Genetic Algorithm (GA), and the Successive Projections Algorithm (SPA) were used. The most satisfactory models achieved sensitivity and specificity rates of 100% for all classes, both for E. coli and for K. pneumoniae. This finding demonstrates that the proposed methodology has promising potential in routine analyzes, streamlining the results and increasing the chances of treatment efficiency. The Enterobacteriaceae family is one of the most clinically prominent bacteria groups. One of the main gramnegative pathogen is Klebsiella pneumoniae (K. pneumoniae), which causes opportunistic infections, such as pneumonia, sepsis and inflammation of the urinary tract 1. Another gram-negative that compose the entereobacteriaceae family is Escherichia coli, which are not typically pathogenic to humans and have the ability to cause several diseases in different sites including gastrointestinal tract, the renal system and the central nervous system 2,3. Antibiotic therapy induces the selection of resistant bacteria 4 , which generate environmental and health hazards, and economical risk. Over the last decades, several bacterial strains have become progressively resistant to antimicrobial agents 5. Bacteria may have natural or acquired resistance. Among the genetic variations that confer resistance in bacteria, the main ones are extended spectrum betalactamases 6 (ESBL), AmpC production, Carbapenemases production 7 , KPC group and MBL group 5. Currently, the standard detection method is culture-based, which is time-consuming and labor intensive, providing a slow detection 8. Other methods can be used to obtain faster results, such as low cytometry 9 , electrochemical detection 10 , and polymerase chain reaction (PCR) 11. Near infrared (NIR) 12 , Raman 13 and Fourier transform infrared (FTIR) spectroscopy 14 have been also reported for these applications.

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“…5 Klebsiella pneumoniae causes pneumonia, sepsis, and inflammation of the urinary tract. 6 E. coli also cause diseases in the intestinal tract, renal system, and central nervous system. 5 AMR is a global challenge, and it is estimated that 1.2 million people die from drug-resistant infections.…”

mentioning

confidence: 99%

Novel antimicrobial finishing of organic cotton fabrics using nano-emulsions derived from Karanja and Gokhru plants

Venkatraman

Sayed

Parte

et al. 2022

Textile Research Journal

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Plant-based antimicrobial finishing of textiles is comparable in efficacy, can replace synthetic antimicrobial agents, and is environmentally safe and effective. However, developing durable antimicrobial finishes on cotton-based textiles is a challenge. This research reports the development and characterization of nano-emulsions obtained from Karanja [ Milletia pinnata] and Gokhru [ Pedalium murex Linn] plants. The nano-emulsions were produced using Milletia pinnata, coconut oil, and curry leaves (nano-emulsion 1) and Pedalium murex, coconut oil, and curry leaves (nano-emulsion 2). The nano-emulsions were characterized for their thermal stability, particle size, pH, and percentage add-on. Two different oils, with surfactant (polysorbate) ratios [1:1 and 1:2], were finished on organic cotton fabrics using a batch process. Scanning electron microscopy images were evaluated to determine the surface morphology of the finished fabrics, and gas chromatography-mass spectrometry images of nano-emulsions were studied to determine the specific chemical constituents of nano-emulsions 1 and 2. The finished fabrics were evaluated for their antimicrobial resistance using various gram-positive bacteria [ Staphylococcus aureus, Staphylococcus epidermidis], which are found on human skin and cause nosocomial infections, gram-negative bacteria [ Escherichia coli and Klebsiella pneumoniae], which cause urinary tract infections, and fungi [ Aspergillus niger]. The antimicrobial resistance was in the range of 98.62–99.87%, even after 10 washes, indicating that the finishes were effective and durable. The finished and unfinished fabrics were also evaluated for their performance properties, tensile strength, and moisture vapor transmission rate, and the results indicated good durability and comfort characteristics. Our findings highlight the potential of plant-based antimicrobial agents for durable finishing of cotton textiles with antimicrobial properties, thus preventing the spread of infections.

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Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae

Cited by 5 publications

References 22 publications

Chemical Synthesis and Antigenicity Evaluation of Shigella dysenteriae Serotype 10 O-Antigen Tetrasaccharide Containing a (S)-4,6-O-Pyruvyl Ketal

Chemical Synthesis and Antigenicity Evaluation of Shigella dysenteriae Serotype 10 O-Antigen Tetrasaccharide Containing a (S)-4,6-O-Pyruvyl Ketal

Identification of resistance in Escherichia coli and Klebsiella pneumoniae using excitation-emission matrix fluorescence spectroscopy and multivariate analysis

Novel antimicrobial finishing of organic cotton fabrics using nano-emulsions derived from Karanja and Gokhru plants

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