By Amelia Pilar Rauter, Thisbe Lindhorst, Yves Queneau, M. Philippe, Jacques Auge, Valerie Molinier, Mattieu Sauthier, Yves Chapleur, Jean-Marie Beau, Qian Wan, Marie-Christine Scherrmann, Richard Daniellou, Jose Kovensky, Slawomir Jarosz, Jean-Maurice Malle
Volume forty of Carbohydrate Chemistry: Chemical and organic methods demonstrates the significance of the glycosciences for innovation and societal development. Carbohydrates are molecules with crucial roles in biology and likewise function renewable assets for the iteration of recent chemical compounds and fabrics. Honouring Professor André Lubineau’s reminiscence, this quantity resembles a unique choice of contributions within the fields of eco-friendly and low-carbon chemistry, leading edge artificial method and layout of carbohydrate architectures for medicinal and organic chemistry.
Green technique is illustrated through bills at the commercial improvement of water-promoted reactions (C-glycosylation, cycloadditions) and the layout of eco-friendly methods and synthons in the direction of sugar-based surfactants and fabrics. The specially demanding ameliorations on the anomeric middle are provided in different contributions on glycosylation methodologies utilizing iron or gold catalysis, electrochemical or enzymatic (thio)glycosylation, exo-glycal chemistry and bioengineering of carbohydrate synthases. Then, synthesis and constitution of multivalent and supramolecular oligosaccharide architectures are mentioned and concerning their actual homes and alertness capability, e.g. for deepening our realizing of organic strategies, akin to enzymatic pathways or bacterial adhesion, and layout of antibacterial, antifungal and leading edge anticancer vaccines or drugs.
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Extra resources for Carbohydrate Chemistry: Volume 40
2 equiv) in ethanol. After 12h, the reaction mixture was quenched with aqueous HCl (1N), and the aqueous phase was extracted with butanol. The organic phase was dried and concentrated in vacuo, to aﬀord the compound. The structure of the C-glycosyl compounds was confirmed by NMR and mass spectroscopy. A. A. Wismeijer, A. P. G. Kieboom and H. Van Bekkum, React. Kinet. Catal. , 1985, 29, 311. General experiment procedures : Normal human dermal fibroblast (NHDF) monolayers were cultured in control medium with or without TGF-b (10ng/ml) or compounds X-Y for 72 hours at 37 1C in humid atmosphere of 95% air and 5% CO2 and labeled with 35S- sulfur during the final 24 hours.
Lerouge, Anal. , 2010, 82, 2893; and (b) C. A. Carpenter, J. A. Kenar and N. P. J. , 2010, 12, 2012. (a) S. Nagarajan and T. Mohan Das, Carbohydr. , 2009, 344, 1028; and (b) S. Nagarajan, P. Arjun, N. Raaman and T. Mohan Das, Carbohydr. , 2010, 345, 1988. P. Stepanek, O. Simak, Z. Novakova, Z. Wimmer and P. Drasar, Org. Biomol. , 2011, 9, 682. 30 | Carbohydr. , 2014, 40, 11–30 How the polarity of carbohydrates can be used in chemistry Rui Xua,b and Yves Queneau*a,b,c 12/04/2014 11:51:22. 1039/9781849739986-00031 Carbohydrates are the polar stars of sustainable chemistry.
1039/9781849739986-00011 Scheme 6 O MeO R Hon43 O avenaciolide O O Cl N O N O N N NH2 OH OH O Olivo41 (–)- homoCarbovir 1 R OH O O O O DIBAL-H OH O O HO O OH OH OH R LiAlH4 Roberts 32b : (+)-BrefeldinA 2 OH OH OH Pd HO O OH O 4 3 OH N t-Bu N N Rhee36 (1S, 2R)-guanine OH analogues OH HO NH H2N N HOOC O HO HO OH Aggarwal44 polyoxin C O HO Rhee37 (–)carbaguanine HN HO HO O OH Carba nucleosides N O N N N NH2 O NH2 NH OH N O Grieco 40 (+ /–)-sesbanimide A HO HO N O N HO O O Roberts36 Mevinic acid N N N Toyota38 (+/–)-epinor-BCA OTMD Fourrey 39 carba DNA NH N Roberts35 NH2 (–)-carbovir NP O CN Scheme 7 Concerning the asymmetric approach, Jorgensen has published a series of articles dealing with the use of copper(II) bisoxazoline as asymmetric catalyst of the HDAR27 and the ene-reaction28 with glyoxylate esters.