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Automated Carbohydrate Synthesis. The Practitioner's Manual

  • Book

  • 300 Pages
  • January 2019
  • John Wiley and Sons Ltd
  • ID: 4469828
Carbohydrate chemistry is one of the challenges facing many organic chemists and biochemists today. It is much more variable than nucleic acids chemistry, for example, making a universal approach impossible. Automation provides a rapid way to speed up synthesis of the desired structures.
Written by one of the leaders in the field of solid–phase carbohydrate synthesis, this practical book covers applications ranging from vaccines to cell signaling, synthetic peptides and asymmetric synthesis. Readers will be able to speed up their carbohydrate synthesis using automation and select the right protocol to efficiently plan synthetic pathways. In addition, a whole section is devoted to case studies, while the book finishes with a conclusion and outlook for the future.
The accompanying CD contains the analytical data for carbohydrate structures for easy access. After earning his PhD in biochemistry in 1995, Peter Seeberger carried out postdoc research with Samuel J. Danishefsky. He began his independent career at MIT in 1998 where he was appointed Firmenich Associate Professor of Chemistry in 2002. One year later he became Professor for Organic Chemistry at the Swiss Federal Institute of Technology (ETH) in Zurich, and Affiliate Professor at the Burnham Institute in La Jolla, CA. Among his many awards, he received the Edgerton Award, the Horace B. Isbell Award from the ACS and the Otto–Klung Weberbank Prize. Prof Seeberger′s research interests focus in particular on the role of complex carbohydrates and glycoconjugates in information transfer in biological systems and on the automation of solid–phase synthesis of carbohydrates and glycosaminoglycans. Daniel B. Werz studied chemistry at the University of Heidelberg, Germany, and the University of Bristol, UK. After gaining his doctorate in physical organic chemistry he joined Peter Seeberger′s group at the ETH as a postdoc fellow in 2004. His research interests focused on the total synthesis of oligosaccharides by solution– and solid–phase methods. Since 2006 he has been an Emmy Noether junior research group leader in the field of synthetic carbohydrate chemistry at the University of Göttingen, Germany. Among several fellowships he received the Ruprecht Karls Award of the University of Heidelberg and the Klaus Grohe Award of the German Chemical Society.

Table of Contents


Carbohydrates in Biology and Medicine

Chemical Synthesis of Carbohydrates

Automated Solid Phase Assembly of Oligosaccharides

Synthesis of Building Blocks

Synthesis of Resins and Linkers

Setup of the Automated Synthesizer

Cleavage of the Oligosaccharide from Resin and

Deprotection and Purification of the Final Product
Removal of the Protecting Groups

Analysis, Quality Control and Quantification of Synthetic Oligosaccharides

Case Studies

Placement of Linkers

Conclusion and Outlook


Peter H. Seeberger Daniel B. Werz