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1

Glikozylacja z zastosowaniem pochodnych 1-tiocukrów jako substratów

Szeja W., Bugla J., Niemiec A., Pastuch G., Kasprzycka A., Ślusarczyk A., Wandzik I., Bieg T., Przybysz B., Bogusiak J.

Wiadomości Chemiczne

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2002

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[Z] 56, 7-8

605-625

EN

It was found that carbohydrate part of complex glycosides may act as antigens or receptors for proteins, and these findings led to the discovery of the important role of carbohydrates in cell-cell recognition phenomena and cell differentiation. At the same time the methods of glycosylation underwent rapid development. The present paper gives an overview of development of 1-thiosugar derivatives in oligosaccharide synthesis. In the first part of this review, recent results of the use of thioglycosides, dithiocarbonates, dithiocarbamates and thiophosphates as glycosyl donors and acceptors are presented. A survey of important methods for the synthesis of thiosugars is presented, followed by discussion of methods converting anomeric substituent into a good leaving group (activation) in nucleophilic substitution reaction. The mechanism and procedures, which provide stereoselective formation of 1,2-cis and 1,2-trans glycoside bond, are discussed. The versatility of 1-thiosugar derivatives in synthetic carbohydrate chemistry is illustrated by selective activation strategies. The most important synthetic methodologies of the synthesis of oligosaccharides like linear glycosylation strategy in step-by-step and multistep "one-pot" sequence, "armed-disarmed" glycosyl donor, "latent-active" glycosylation, orthogonal strategy are illustrated on several examples. The last part is devoted to methods for solid support oligosaccharide synthesis.

2

Synthesis of Glycofuranosides

Bogusiak J.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 1

1-12

EN

Glycofuranosides are ubiquitous in biological structures, playing important functions in immunological response and bacterial or viral infection [1,2]. To elucidate their biological functions and their possible use in therapy, there are more and more attempts to synthesize smaller or bigger structures (glycosides, oligosaccharides, glycoconjugates) containing furanosyl units. This article describes recent advances in the development of efficient synthesis methods for glycofuranosides.

3

Convenient Synthesis of Glycofuranosyl Azides

Bogusiak J.

Polish Journal of Chemistry

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2000

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Vol. 74, nr 4

503-507

EN

Glucofuranosyl azides, derivatives of L-arabino-, D-ribo- and D-xylofuranose were prepared by treatment of reducing monosaccharides with diphenyl phosphorochloridate or tosyl chloride and sodium azide under phase-transfer conditions, while mannofuranosyl azide can be easily obtained only in reaction with tosyl chloride.

4

Synthesis and application of S-glycofuranosyl O,O-dietyl phosphorodithioates

Bogusiak J.

Polish Journal of Chemistry

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1999

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vol. 73 nr 4

619-623

EN

S-Glycosol O, O-diethyl phosphorodithioates derivatives of L-arabino-, D-ribo- and D-xylofyranose can be conveniently prepared by treatment of reducing monosaccharides with tosyl chloride or diphenyl phosphorochloridate and diethyl phosphorodithioate under phase-transfer conditions. Their ability to act as glycosyl donors was demonstrated.