By Peter Grunwald
Content material: 1. fundamentals in carbohydrate chemistry / Heinrich Hühnerfuss -- 2. Glycoconjugates : a quick evaluate / Peter Grunwald -- three. Oligosaccharides and glycoconjugates in reputation procedures / Thisbe okay. Lindhorst -- four. Glycoside hydrolases / Motomitsu Kitaoka -- five. Disaccharide phosphorylases : mechanistic variety and alertness within the glycosciences / Christiane Luley-Goedl and Bernd Nidetzky -- 6. Enzymatic and chemoenzymatic synthesis of nucleotide sugars : novel enzymes, novel substrates, novel items, and novel routes / Leonie Engels and Lothar Elling -- 7. Iteratively performing glycosyltransferases / Marta Luzhetska and Andreas Bechthold -- eight. Bacterial glycosyltransferases eager about molecular mimicry of mammalian glycans / Warren Wakarchuk -- nine. Sulfotransferases and sulfatases : sulfate amendment of carbohydrates / Eli Chapman and Sarah R. Hanson -- 10. Glycosylation in well-being and ailment / Peter Grunwald -- eleven. Sialic acid derivatives, analogues, and mimetics as organic probes and inhibitors of sialic acid spotting proteins / Joe Tiralongo and Thomas Haselhorst -- 12. Enzymes of the carbohydrate metabolism and catabolism for chemoenzymatic syntheses of complicated oligosaccharides / Julian Thimm and Joachim Thiem -- thirteen. From gene to product : tailored oligosaccharides and polysaccharides via enzyme and substrate engineering / Jürgen Seibel -- 14. Synthesis and amendment of carbohydrates through metabolic pathway engineering in microorganisms / Xian-wei Liu ... [et al.] -- 15. Metabolic pathway engineering for hyaluronic acid creation / Esteban Marcellin, Wendy Y. Chen, and Lars ok. Nielsen -- sixteen. Microbial rhamnolipids / Markus M. Müller ... [et al.] -- 17. Chitin-converting enzymes / Karin Moss ... [et al.] -- 18. Linear and cyclic oligosaccharides / Hajime Taniguchi -- 19. Fungal degradation of plant oligo- and polysaccharides / Ronald P. de Vries ... [et al.] -- 20. Bacterial concepts for plant telephone degradation and their genomic details / Yutaka Tamaru and Roy H. Doi -- 21. layout of effective multienzymatic reactions for cellulosic biomass processing / Anne S. Meyer
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Extra info for Carbohydrate-modifying biocatalysts
These two rules can lead to didactic disasters according to the present author’s experience: if students have to convert the Haworth projection formulae to the realist chair configuration, they often misinterpret the Haworth rules and assume an all-axial direction of the HO groups in glucose. Because of this didactic misunderstanding, the present author warns about applying the Haworth projection in basic courses of organic chemistry and refrains from showing them in this chapter. 2 Disaccharides Further reaction of the hemiacetal group of a cyclic monosaccharide with another alcohol group of a second monosaccharide leads to an acetal group, in this case referred to as a glycoside.
One well-defined diastereomer is obtained. 17 Catalytic hydrogenation of d-glucose. H HO H H OH H OH OH CH2OH DǦGlucitol In contrast, the reduction of a ketose supplies two diastereomers, because a new stereogenic centre is generated. This is Reactions of Carbohydrates shown in Fig. 18 for the reduction of d-fructose by NaBH4. Thus the same reduction product d-glucitol is accessible, as obtained by reduction of d-glucose; however, the C2 epimer d-mannitol is obtained as well. d-Glucitol, which is also called sorbitol, is found in cherries, pears, plums, and several berries.
However, some special modifications of the typical reaction characteristics may be observed. For example, aldehydes and ketones may react with one equivalent of phenylhydrazine, thus forming phenylhydrazones. In the case of aldoses and ketoses, three equivalents of phenylhydrazone have to be applied. If two equivalents of phenylhydrazine were used, the reaction would lead to imines, and the reaction stops at this point. Adequate reaction conditions are depicted in Fig. 19, which shows that one equivalent of phenylhydrazine is assumed to react as an oxidizing agent, thereby being reduced to aniline and ammonia.