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Recent Trends in Carbohydrate Chemistry: Synthesis and Biomedical Applications of Glycans and Glycoconjugates [Pehme köide]

Edited by (NOBIPOL - Department of Biotechnology and Food Science), Edited by , Edited by (Department of Organic Chemistry, University of Debrecen, Hungary), Edited by (Faculty of Sciences, University of Lisbon), Edited by (University of Natural Resources and Life Sciences in Vienna, Aus)
  • Formaat: Paperback / softback, 438 pages, kõrgus x laius: 229x152 mm, kaal: 680 g
  • Ilmumisaeg: 29-Apr-2020
  • Kirjastus: Elsevier Science Publishing Co Inc
  • ISBN-10: 0128209542
  • ISBN-13: 9780128209547
Teised raamatud teemal:
  • Formaat: Paperback / softback, 438 pages, kõrgus x laius: 229x152 mm, kaal: 680 g
  • Ilmumisaeg: 29-Apr-2020
  • Kirjastus: Elsevier Science Publishing Co Inc
  • ISBN-10: 0128209542
  • ISBN-13: 9780128209547
Teised raamatud teemal:

Recent Trends in Carbohydrate Chemistry: Synthesis and Biomedical Applications of Glycans and Glycoconjugates covers biomedically relevant bacterial cell wall carbohydrates including recent findings on biosynthetic aspects, advances in the chemical assembly of bacterial lipopolysaccharide fragments and teichoic acids, and modern NMR approaches to unravel structural details. The first part introduces and provides the relevant background for synthetic glycoconjugate vaccines. The second section focuses on synthetic carbohydrate-based vaccines of therapeutic potential that are licensed or under development.

This second volume of Recent Trends in Carbohydrate Chemistry is ideal for researchers working as synthetic organic chemists, as well as those interested in glycoconjugation, protein chemists, immunologists, and microbiologists, in academia as well as in industry.

  • Highlights important features of bacterial glycoproteins

  • Illustrates modern chemical synthesis and structural analysis of bacterial glycans

  • Demonstrates the importance of carbohydrate chemistry for the synthesis of lipopolysaccharides and teichoic acid

  • Covers recent findings on glycan ligation

  • Gives an overview of the most recent developments on carbohydrate-based vaccines

Contributors ix
Preface xi
Part One Advances in chemical synthesis and biosynthesis of bacterial glycans
1(282)
1 Prokaryotes: Sweet proteins do matter
3(34)
Christina Schaffer
Paul Messner
1 Introduction
3(2)
2 Cell surface (S-) layer glycoproteins
5(1)
3 Bacteria
6(11)
4 Flagella/Archaella and fimbriae
17(2)
5 Adhesins, bacteriocins, invasins, and glycocins
19(6)
6 Spores
25(1)
7 Concluding remarks
25(2)
References
27(10)
2 Glycan ligation reactions in the periplasmic space
37(14)
Miguel A. Valvano
1 Introduction
37(2)
2 WaaL O-antigen ligases
39(2)
3 The ArnT family
41(2)
4 Oligosaccharyl transferases
43(1)
5 Conclusions
44(1)
References
45(6)
3 Synthesis of bioactive lipid A and analogs
51(52)
Alia Zamyatina
Sebastian Strobl
1 Lipid A---Structure, immunobiological function, and potential therapeutic significance
52(8)
2 Synthesis of lipid A and analogs
60(17)
3 Application of lipid A derivatives as vaccine adjuvants
77(4)
4 Synthesis of lipid A modified by addition of amino sugars at the glycosidic phosphate group
81(8)
5 Conclusion
89(1)
References
89(14)
4 Synthesis of lipopolysaccharide core fragments
103(40)
Paul Kosma
1 Introduction
103(1)
2 Synthesis of LPS inner core fragments
104(26)
3 Synthesis of outer core fragments
130(4)
4 Conclusions
134(1)
Acknowledgment
134(1)
References
134(9)
5 Synthesis of oligosaccharides related to potential bioterrorist pathogens
143(64)
Maude Cloutier
Kevin Muru
Charles Gauthier
1 Introduction
143(1)
2 Bacillus anthracis
144(29)
3 Burkholderia pseudomallei and Burkholderia mallei
173(9)
4 Francisella tularensis
182(4)
5 Yersinia pestis
186(6)
6 Brucella spp.
192(7)
7 Conclusion
199(1)
References
199(8)
6 Synthetic teichoic acid chemistry for vaccine applications
207(32)
Sara Ali
Francesca Berni
Jacopo Enotarpi
Gijs A. van der Marel
Jeroen D.C. Codee
1 Introduction
207(2)
2 Synthetic teichoic acids
209(24)
3 Conclusions
233(3)
References
236(3)
7 NMR characterization of bacterial glycans and glycoconjugate vaccines
239(44)
Neil Ravenscroft
Francesco Berti
1 NMR characterization of carbohydrates
240(9)
2 NMR analysis of surface carbohydrates of gram-negative bacteria
249(8)
3 NMR analysis of surface carbohydrates of gram-positive bacteria
257(10)
4 NMR analysis of glycoconjugate vaccines
267(7)
5 Investigating antigen-antibody interactions using NMR spectroscopy
274(2)
6 Conclusions
276(1)
Acknowledgments
276(1)
References
276(7)
Part Two Synthetic carbohydrate-based vaccines: present and future
283(130)
8 Glycoconjugate vaccines, production and characterization
285(30)
Ralph Biemans
Francesca Micoli
Maria Rosaria Romano
1 Introduction
285(4)
2 Conjugation chemistries
289(8)
3 Physicochemical characterization and quality control of glycoconjugate vaccines
297(4)
4 Conclusions
301(1)
Disclosures
302(1)
References
302(13)
9 Antifungal glycoconjugate vaccines
315(20)
Paolo Costantino
1 Introduction
315(1)
2 Major human fungal pathogens
316(1)
3 Carbohydrates in the molecular architecture of fungal CWs
317(1)
4 Immunity against fungal pathogens
317(2)
5 Glycoconjugates as antifungal vaccines
319(5)
6 Glycoconjugates vaccines against Candida
324(1)
7 Mannan glycoconjugates
324(1)
8 β-Glucan glycoconjugates
325(1)
9 Poly-N-acetyl-(l→6)-α-glucosamine glycoconjugates
326(1)
10 Glycoconjugates vaccines against Aspergillus fumigatus
327(1)
11 Glycoconjugates vaccines against Cryptococcus neoformans
327(2)
12 Conclusion
329(1)
References
330(5)
10 Site-selective conjugation chemistry for synthetic glycoconjugate vaccine development
335(46)
Omar Boutureira
1 Introduction
335(1)
2 Homogeneous glycoprotein vaccine design
336(24)
3 Conclusions and outlook
360(1)
Acknowledgments
360(1)
References
360(21)
11 Glyconanoparticles as versatile platforms for vaccine development: A minireview
381(32)
Laura Polito
1 Glyconanoparticles based on inorganic core
384(12)
2 Glyconanoparticles based on polymeric core
396(1)
3 Glyconanoparticles based on self-assembling core
397(2)
4 Glyconanoparticles based on OMVs
399(2)
5 Glyconanoparticles based on virus-like particles
401(2)
6 Conclusions
403(1)
References
403(10)
Index 413
Professor of Organic Chemistry since 1984; Professor of Carbohydrate Chemistry in the Faculty of Sciences, University of Lisbon (3rd year course of the Graduation in Chemistry since 2001), editor of the RSC book series Carbohydrate Chemistry Chemical and Biological Approaches (since 2008); Guest editor of Wiley Eur J Org Chem., vol 2013(8) and the book Carbohydrate Mimics (1998); of Springer - Topics in Current Chemistry, vols 294, 295 in 2010; of DeGruyter Pure and Applied Chemistry (vol 89(7) in2017 and vol 88(4) in2016); Ph.D. in Carbohydrate Chemistry (TU Graz, Austria); Expert in monosaccharide chemistry (deoxygenation, Wittig olefination, domino reactions, C-glycosylation, nucleoside synthesis, glycomedicinal chemistry), with more than 150 publications in the area, 15 book chapters and 10 granted patents. Bjørn E. Christensen holds a Dr. philos. degree in biotechnology from NTNU - Norwegian University of Science and Technology, Norway, where he also had a career as research scientist until 2002 when he became a full professor. His research field is polysaccharide engineering and includes studies of macromolecular characterisation and structure-function relationships in among other alginates, chitosans, pectins, xanthan and -1,3-glucans. He has also been visiting scientist/professor at Montana State University, USA (1985), Osaka Prefecture University, Japan (2009), Cermav-CNRS Grenoble, France (2010) and University of Bordeaux, France (2016). Full professor, former director of the Institute of Chemistry and head of the Department of Organic Chemistry of the University of Debrecen, Hungary. Serves as an editorial board member for Carbohydrate Research, and as guest editor for special issues of Carbohydrate Research, Mini-Reviews in Medicinal Chemsitry, Molecules, Topics in Heterocyclic Chemistry. Research interests include synthetic carbohydrate chemistry directed to C-glycosyl compounds, anomeric-spirocycles, glycals, exo-glycals and their derivatives; development of synthetic methodology involving radicals and carbenes; synthesis of glycosidase and glycogen phosphorylase inhibitors as potential antidiabetics, study of their structure-activity relationships; synthesis of glycomimetics and glycopeptidomimetics. Dr. Paul Kosma is a full professor at the University of Natural Resources and Life Sciences in Vienna, Austria. He also serves as head of the Institute of Organic Chemistry and Deputy of the Department of Chemistry. His areas of expertise include organic synthesis, NMR spectroscopy, complex carbohydrates, Natural Product Synthesis and Chemistry of Triterpenes. He has published hundreds of journal articles and conference proceedings, served on the editorial boards of international journals, chaired a dozen international conferences, and supervised 35 theses in his career. Roberto Adamo obtained his PhD in Pharmaceutical Science from the University of Catania (Italy) in 2003, with a thesis on the synthesis of biologically relevant inositols. He was post-doctoral fellow at the NIH in Bethesda (USA), under the supervision of Dr. P. Kovac, and then in the group of Prof. J. P. Kamerling at the Utrecht University (The Netherlands). In 2007 he joined Novartis Vaccines where he was later apoointed Head of the Carbohydrate Chemistry Laboratory, and Leader of the Conjugation & Synthesis Platform. Following the company acquisition by GSK he became Preclinical Representative Leader of the Conjugation Platform. His research interests focus on the synthesis of glycans, glycoconjugates and glyconanoparticles to be used for carbohydrate-based therapeutics. He has been recently appointed Conjugation Technology Platform Leader at GSK, covering chemical and glycoengineering approaches for glycoconjugate vaccines. He is associate editor in the Glycoconjugate Journal and Coordinator of the EU network Glycovax.