structural aspects of carbohydrates and the relation with their biological properties

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g biological properties, predominantly those that can be used in medical chemistry. the diversity of biological properties of saccharides are surprisingly large spanning from sources of energy in living systems, to cell adhesion, growth and differentiation, anti- inflammatory and anticoagulant properties, angiogenesis, etc [1]. this large variety of properties originates from the structural arrangement of carbohydrates. carbohydrates can form linear polymeric forms, like the previously mentioned cellulose, but also very complex branched structures or conjugates with other type of molecules, most importantly, proteins. in glyco-conjugates, e.g. glyco-proteins, the saccharide part can be very small (consisting of even a single monosaccharide unit) up to conjugates where the saccharide part is larger than the protein structure itself. the structure of monosaccharides, pyranoses or furanoses, allows creation of linkages in various positions. for example, hexopyranoses can be linked with other monosaccharides in positions 1, 2, 3, 4 and 6 (chart 1), thus a …

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nd originates from their complex constitution. the overall conformation is determined predominantly by the stereochemistry at glycosidic linkages, conformation of pendant groups and the pseudorotation of pyranose and furanose rings. as carbohydrates are nearly exclusively present in the ring forms, stereo-chemical arrangement of carbohydrates is affected by ring puckering [2]. pyranoses adopt the 4c1 (chart 1) or 1c4 chair forms in most cases whereas other conformations are relatively rare. however, large substituents can have a pronounced influence on the ring conformation and the boat or the skew conformers can be present in substituted derivatives. furanose forms are more flexible with respect to pyranose forms and the populations of conformers depend on the structure of neighboring units and substitution. this is also valid for deoxy derivatives, such as 2-deoxy-β-d-erythro-pentose, which is the component of dna structure. furthermore, both d and l forms exist in oligo- and polysaccharides, the d form being …

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conformation in hexopyranoses, such as glucose or mannose [2, 3]. arrangements of other pendant groups, such as o-acetyl, n-acetyl, carboxylate, n-sulfate, etc. have not been studied in details. relatively little knowledge about the conformational equilibriums of hydroxyl groups though their conformations are crucial for understanding of hydrogen bonds formation (intra- or intermolecular) or recognition processes. h o5 h c5 c4 o6 h h o5 h c5 c4 o6 h h o5 h c5 c4 o6 h ω = -60o ω = 60o ω = 180o chart. (2). probably the most complicated, and the most discussed, is conformation at the glycosidic linkages. the mutual orientation of neighboring saccharide units is described by the torsion angles φ, ψ (φ = o-5’-c-1’-o-1’-c-x; ψ= c-1’- o-1’-c-x-c-x-1) (chart 3); the orientation defined by φh, ψh (φh = h-1’-c-1’-o-1’-c-x; ψh = c-1’-o-1’-c-x-h-x) is also often presented in literature and will be used in the present paper. …

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hricov.ni_cmc see discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/8183474 structural aspects of carbohydrates and the relation with their biological properties article in current medicinal chemistry · november 2004 doi: 10.2174/0929867043364414 · source: pubmed citations 40 reads 1,480 1 author: miloš hricovíni slovak academy of sciences 88 publications 2,027 citations see profile all content following this page was uploaded by miloš hricovíni on 20 march 2017. the user has requested enhancement of the downloaded file. https://www.researchgate.net/publication/8183474_structural_aspects_of_carbohydrates_and_the_relation_with_their_biological_properties?enrichid=rgreq-3dec5c679090530b31e56a85a580930a-xxx&enrichsource=y292zxjqywdlozgxo...

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