Carbohydrates novel structures

L. Hough, A. C. Richardson, and L. A. W. Thelwall, Reaction of lactose with 2,2-dimethoxypropane. A tetra-acetal of novel structure, Carbohydr. Res., 75 (1979) C11-C12. 

D-Apiose can be isolated from parsley and is a component of the cell wall polysaccharide of various marine plants. Among its novel structural features is the presence of only a single chirality center. L-Vancosamine is but one portion of vancomycin, a powerful antibiotic that has emerged as one of only a few antibiotics that are effective against drug-resistant bacteria. L-Vancosamine is not only a branched-chain carbohydrate, it is a deoxy sugar and an amino sugar as well. 

Hydrocortisone and Prednisolone. Following the discovery of the antiinflammatory actions of cortisone (1) and cortisol (2), there was a need not only to develop highly efficient routes to the corticoids, but to discover novel structures with fewer side effects than those of the corticoids, eg, sodium and water retention, reduced carbohydrate tolerance (steroid diabetes), osteoporosis, and depressed host defense. 

Owing to the great impact that p.m.r. spectroscopy has made on structural carbohydrate chemistry, it is not feasible to discuss here all of the reports in which this technique has been used merely to confirm assigned structures. In the present Chapter, some selectivity has been exercised in favor of novel structural and conformational applications, innovative techniques, information that could not be obtained by other methods, and a fundamental understanding of the magnetic parameters of carbohydrate molecules. 

J. Bouckaert, T. Hamelryck, L. Wyns, and R. Loris. 1999. Novel structures of plant lectins and their complexes with carbohydrates Curr. Opin. Struct. Biol. 9 572-577. (PubMed)... 

Bouckaert. J., Hamelryck. T., Wyns. L.. and Loris, R. 1999. Novel. structures of plajit lectins and their complexes with carbohydrates. Curr. Opin Struct Biol. 9 572 577. 

Studies on cyanobacterial monogalactosyl- and digalactosyldiacylglycer-ols are reported in particular from Phormidium tenue [104-106] and Fischer-ella ambigua [107]. Some of the products from P. tenue showed potent inhibitory activity towards tumor promotion (in in vitro assay of Epstein-Barr virus activation in Raji cells induced by 12-O-tetradecanoylphorbol-13-acetate). Additional novel structures with difference in carbohydrate backbone and fatty acid moieties have been published for glycoglycerolipids of Rhodobacter sphaeroides [108], Saccharopolyspora sp [109], Thermus aquaticus [110], the sponge-associated bacterium Micrococcus luteus [111], Arthrobacter atrocyaneus [112], and from the Mycobacterium avium-intra-cellulare complex [113]. 

The groundwork has now been laid for the exploitation of f.a.b.-m.s. by all carbohydrate chemists involved with the structural analysis of novel compounds. There is no reason why f.a.b.-m.s. should not take its place alongside g.l.c.-m.s., e.i.-m.s., and c.i.-m.s. as a relatively routine, analytical procedure. It is important, however, that f.a.b.-m.s. be integrated into sensible structural strategies, and that it be very closely linked to the chemical manipulations that are also being conducted as part of the structural program. 

Nobmann P, Smith A, Dunne J, Henehan G and Bourke P. 2009. The antimicrobial efficacy and structure activity relationship of novel carbohydrate fatty acid derivatives against Listeria spp. and food spoilage microorganisms. Int J Food Microbiol 128(3) 440—445. 

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