Carbohydrate-based synthetic

Koganty, R.R., Reddish, M.A., and Fongenecker, B.M. (1996) Glycopeptide- and carbohydrate-based synthetic vaccines for the immunotherapy of cancer. Drug Disco. Today, 1, 190-198. 

Carbohydrate-based synthetic polymers can be prepared by polymerization of small, activated carbohydrate-derived monomers. A pioneering study in this field was the preparation and polymerization26 of methyl 2,3,4,6-telra-O-allyl-a-D-glucopyranoside (1). Under the influence of oxygen and heat, compound 1 gradually polymerizes, first to a viscous liquid and finally to a colorless, transparent resin. Similarly, acrylate and... 

K.-C. Chu and C.-Y. Wu, Carbohydrate-Based Synthetic Vaccines Does the Synthesis of Longer Chains of Carbohydrate Make This a Step over Closer , Future Med. Chem., 2012, 4, 1767. 

A carbohydrate-based synthetic approach has provided unambiguous evidence for the structure of ascidiatrienolide A 73 (Scheme 14). When first isolated (in 1989), this macrocyclic lactone was originally assigned structure 72 containing a 9-membered ring. Holmes has used key intermediate 69 to prepare both of the macrocyclic components 70 and 71 which have been carried through to 72 and 73 respectively. ... 

Nowadays, a strategic area of research is the development of polymers based on carbohydrates due to the worldwide focus on sustainable materials. Since the necessary multi-step synthesis of carbohydrate-based polymers is not economical for the production of commodity plastics, functionalization of synthetic polymers by carbohydrates has become a current subject of research. This aims to prepare new bioactive and biocompatible polymers capable of exerting a temporary therapeutic function. The large variety of methods of anchoring carbohydrates onto polymers as well as the current and potential applications of the functionalized polymers has been discussed recently in a critical review [171]. Of importance is that such modification renders not only functionality but also biodegradability to the synthetic polymers. 

L. L. Kiessling, J. K. Pontrello, and M. C. Schuster, Synthetic multivalent carbohydrate ligands as effectors or inhibitors of biological processes, in C.-H. Wong, (Ed.), Carbohydrate-Based Drug Discovery, Wiley-VCH Weinheim, Germany, 2003, pp. 575-608. 

Rg. 60. Schematic representation of a fully synthetic carbohydrate-based vaccine. 

Some reviews have been published on the synthetic carbohydrate-based polymers and glycopolymers [11-15]. However, they refer mainly to poly(vinylsaccharide)s and other conventional functionalized polymers having sugars as groups pendant from the main chain of the polymer. In this chapter we shall describe those sugar-based monomers which lead to polymers having the sugar units incorporated into... 

Abstract Carbohydrates have been investigated and developed as delivery vehicles for shuttling nucleic acids into cells. In this review, we present the state of the art in carbohydrate-based polymeric vehicles for nucleic acid delivery, with the focus on the recent successes in preclinical models, both in vitro and in vivo. Polymeric scaffolds based on the natural polysaccharides chitosan, hyaluronan, pullulan, dextran, and schizophyllan each have unique properties and potential for modification, and these results are discussed with the focus on facile synthetic routes and favorable performance in biological systems. Many of these carbohydrates have been used to develop alternative types of biomaterials for nucleic acid delivery to typical polyplexes, and these novel materials are discussed. Also presented are polymeric vehicles that incorporate copolymerized carbohydrates into polymer backbones based on polyethylenimine and polylysine and their effect on transfection and biocompatibility. Unique scaffolds, such as clusters and polymers based on cyclodextrin (CD), are also discussed, with the focus on recent successes in vivo and in the clinic. These results are presented with the emphasis on the role of carbohydrate and charge on transfection. Use of carbohydrates as molecular recognition ligands for cell-type specific dehvery is also briefly... 

S. J. Danishefsky and J. R. Allen, From the laboratory to the clinic A retrospective on fully synthetic carbohydrate-based anticancer vaccines, Angew. Chem. Int. Ed., 39 (2000) 836-863. 

Topiramate analogue 168 was enlisted into a comprehensive structural-activity relationship study [37], along with about a hundred varied synthetic analogues, which allowed identification of a new promising antiepileptic lead. From this study, carba-analogue 168 resulted three times more active than its corresponding carbohydrate-based drug. 

Several carbohydrate-based sweeteners exist on the market today. Although sucrose is the gold standard for sweeteners, other sweeteners gain commercial viability because they are less expensive (such as corn-based sweeteners), have fewer calories, or are better suited for diabetic diets. Unlike the synthetic sweeteners, most of the carbohydrate-based... 

McGeary, R. P., Jablonkai, 1., and Toth, I. (2001) Carbohydrate-based templates for synthetic vaccines and drug delivery. Tetrahedron 57, 8733-8742. 

Carbohydrates have long been a source of scientific interest because of their abundance in nature, and to the synthetic challenges posed by their polyhydroxylated structures. However, the commercial use of carbohydrates has been significantly limited by the hydrolytic lability of the glycosidic bond. With the advent of C-glycosides, this limitation promises to be overcome, thus paving the way for a new generation of carbohydrate-based products. 

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