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.

Artykuł - szczegóły

Tytuł artykułu

Glikozylacja z zastosowaniem pochodnych 1-tiocukrów jako substratów

Autorzy

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

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Derivatives of 1-thiosugars as substrates in glycosylation reactions

Języki publikacji

Abstrakty

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.

Słowa kluczowe

tioglikozydy glikozylacja chemia węglowodanów

glycosylation reactions sugars

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2002

Tom

[Z] 56, 7-8

Strony

605--625

Opis fizyczny

schem., bibliogr. 73 poz.

Twórcy

autor

Szeja W.

autor

Bugla J.

autor

Niemiec A.

autor

Pastuch G.

autor

Kasprzycka A.

autor

Ślusarczyk A.

autor

Wandzik I.

autor

Bieg T.

autor

Przybysz B.

autor

Bogusiak J.

Wydział Chemiczny, Politechnika Śląska ul. B.Krzywoustego 8, 44-100 Gliwice

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Typ dokumentu

Bibliografia

Identyfikator YADDA

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