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Oligosaccharide Synthesis in Microreactors

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In linear oligosaccharide synthesis, ..

The Department of Biomolecular Systems developed prior to the arrival in Potsdam at MIT (1998-2003) and at ETH Zürich (2003-2009), by solving a host of chemical problems, the first automated oligosaccharide synthesizer as a platform to pursue glycomics as the next frontier in biology and medicine. This instrument provides now access to many complex carbohydrates in days rather than years. Prototype instruments have been built to achieve these syntheses in a fully automated manner. This platform is currently being expanded to all classes of carbohydrates including glycolipids, glycoproteins, and heparin. All aspects of automated synthesis are being improved as novel methods resulted in excellent efficiency, selectivity and versatility of the synthetic process. The Department is closing in on the ultimate goal of creating a commercially available instrument that uses a defined set of monosaccharide building blocks to assemble most oligosaccharides reliably. Thus, non-specialists will be able to access defined sugars for biological or medical applications.

Development of synthetic processes using microreactorMasashi Oda(Hitachi Plant Technologies, Ltd.)

It is critical to make complex carbohydrates more accessible to general chemical, biochemical, and industrial researchers to keep pace with the exploding area of glycobiology. This aim can only be achieved by the development of methods and strategies for efficient oligosaccharide synthesis that would be applicable for both laboratory and industrial preparation. A number of excellent strategies that offer a reasonably efficient route to oligosaccharide assembly have already emerged and the armed–disarmed approach for chemoselective oligosaccharide synthesis is undoubtedly amongst them. Although recent advancements discussed herein have expanded the scope of the armed–disarmed methodology, it is clear that further development of efficient and general methods for the expeditious synthesis of complex carbohydrates will remain an important and active arena for scientific endeavors during the twenty-first century.

to oligosaccharide synthesis in order to ..

PL-10: Synthetic Biology for Synthetic Chemistry  Jay D. Keasling, University of California, Berkeley, USA

Synthesis of allyl-type heavy fluorous tag and its application for oligosaccharide synthesis (Grad. Sch. Adv. Integration Sci., Chiba Univ.; The Noguchi Institute) º FUKUDA, Kazuo; TOJINO, Mami; GOTO, Kohtaro; DOHI, Hirofumi; NISHIDA, Yoshihiro; MIZUNO, Mamoru

Complex carbohydrates (polysaccharides or complex glycoconjugates in which oligosaccharides are connected to peptides, proteins, or fatty acids) are involved in a variety of biological processes []. Throughout the past two decades, the main scientific effort in the field of glycoscience has remained centered upon those carbohydrates associated with diseases that consistently rank among the leading causes of death worldwide, such as cardiovascular disease, cancer, septicemia, bacterial, viral, and parasitic infections. The driving force behind this tremendous scientific and industrial effort is the belief that a comprehensive knowledge of the structural, conformational, and other general properties of these carbohydrates will help scientists understand the pathogenesis of the associated diseases. Consequently, this could lead to the development of new and effective strategies for the prevention, diagnosis, and treatment of these diseases. Over the years, glycoscientists have mastered the techniques necessary for isolating only certain classes of naturally occurring carbohydrates. Therefore, the availability of pure natural isolates cannot satisfy all of the challenges presented by modern glycoscience. As a result, glycoscientists have turned to both chemical and enzymatic synthesis as a means for accessing complex carbohydrates. While enormous progress in the areas of synthetic, biological, and analytical chemistry has made many classes of organic compounds readily accessible through broadly applicable methods, carbohydrates of even moderate complexity still represent a significant challenge. A few representative examples of such oligosaccharide sequences are shown in .

Oligosaccharide synthesis in microreactors.

High-pressure Synthesis; Microreactors; Microreactors II; Oligosaccharide production;

Figure 2: Adapted from: M.A. Boon et al.(2000) Enzymatic synthesis of oligosaccharides: Product removal during a kinetically controlled reaction. Biotechnol. Bioeng. 70:411-420 In this project we are using an enzymatic synthesis of oligosaccharides as a model system. This model system has to be integrated with a highly specific separation of oligosaccharides, to show the increased conversion of substrate into product. In nature, lectins are common biocomplexants. In a sustainable process the biocomplexants have to be removed from the reaction mixture in order to regenerate the biocomplexant. Immobilization of the biocomplexant on magnetic beads is considered as an option. In this way the complex of biocomplexants and bound product can easily be picked out from the reaction mixture using only magnetic fields. The molecules can easily be transported for regeneration when the magnetic field is switched off (see figure 3). Extremes of pH, chaotropic salts, ionic strength and temperature shocks can dissociate the product from the biocomplexant, mostly by denaturating the biocomplexant. For a sustainable process the product has to be dissociated without denaturating the biocomplexant. Therefore, milder dissociation conditions has to be found.

The Janssen Pharmaceutica Prize for Creativity in Organic Synthesis (formerly Dr Paul Janssen Prize for Creativity in Organic Synthesis) was established in 1986 on the occasion of the first Belgian Organic Synthesis Symposium (BOSS). The Prize is intended to honour Dr Paul Janssen, founder of Janssen Pharmaceutica.

The Prize is awarded on a biennial basis, on the occasion of the BOSS, to a chemist under the age of 50 who has made a significant contribution to the field of organic synthesis in the broadest sense.

Modern Synthetic Methods in Carbohydrate Chemistry: …
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  • to oligosaccharide synthesis in order to find ..

    Modern Synthetic Methods in Carbohydrate Chemistry: From Monosaccharides to Complex ..

  • In Microreactors in Organic Synthesis and ..

    A semi-synthetic oligosaccharide conjugate vaccine candidate confers protection against ..

  • chemical synthesis reactions in microreactors.

    Keywords: acid-mediated reaction; microreactor; natural products synthesis; oligosaccharide; pristane

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Plenary 15 Automated Oligosaccharide Synthesis, Microreactors ..

PL-15: Automated Oligosaccharide Synthesis, Microreactors and Synthetic Vaccines
Peter H. Seeberger
, Max Planck Institute of Colloids and Interfaces, Germany

What are Microreactors in Organic Synthesis

PL-14: Automated Glycan Synthesis Inspired from Biosynthetic Systems and Their Use in Drug Discovery Research
Shin-Ichiro Nishimura, Hokkaido University, Japan

The UCB-Ehrlich Award for Excellence in Medicinal Chemistry

We present a formal calculus, termed the chemtainer calculus, able to capture the complexity of compartmentalized reaction systems such as populations of possibly nested vesicular compartments. Compartments contain molecular cargo as well as surface markers in the form of DNA single strands. These markers serve as compartment addresses and allow for their targeted transport and fusion, thereby enabling reactions of previously separated chemicals. The overall system organization allows for the set-up of programmable chemistry in microfluidic or other automated environments. We introduce a simple sequential programming language whose instructions are motivated by state-of-the-art microfluidic technology. Our approach integrates electronic control, chemical computing and material production in a unified formal framework that is able to mimic the integrated computational and constructive capabilities of the subcellular matrix. We provide a non-deterministic semantics of our programming language that enables us to analytically derive the computational and constructive power of our machinery. This semantics is used to derive the sets of all constructable chemicals and supermolecular structures that emerge from different underlying instruction sets. Because our proofs are constructive, they can be used to automatically infer control programs for the construction of target structures from a limited set of resource molecules. Finally, we present an example of our framework from the area of oligosaccharide synthesis.

furfural, 98-01-1 - The Good Scents Company

The Synthesis of Functional Dyes via 4-component Coupling Reaction and Their Evaluation of Inhibitory Activity against the Aggregation of Amyloid and tau Proteins (Grad. Sch. Sci., Eng., Tokyo Tech; Doshisha Univ. Graduate School of Brain Science; Yokohama Coll. of Pharmacy) º MATSUMURA, Keisuke; FUSE, Shinichiro; FUJITA, Yuki; SUGIMOTO, Hachiro; TAKAHASHI, Takashi

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