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Tytuł oryginału: Syntezy naturalnych i modyfikowanych antybiotyków antracyklinowych ze wspólnego prekursora: 3,4-di-O-acetylo-L-ramnalu.
Tytuł angielski: Syntheses of natural and modified anthracycline antibiotics from a common precursor: 3,4-di-O-acetyl-L-rhamnal.
Autorzy: Grynkiewicz Grzegorz, Achmatowicz Osman, Fokt Iza, Priebe Waldemar, Ramza Jan, Szechner Barbara, Szeja Wiesław
Źródło: Wiad. Chem. 2002: 56 (7/8) s.535-560, il., sum.
Sygnatura GBL: 310,575

Hasła klasyfikacyjne GBL:
  • farmacja
  • onkologia

    Typ dokumentu:
  • praca doświadczalna

    Streszczenie angielskie: While natural anthracycline antibiotics retain their possition of clinically important antitumor drugs despite their serious side effects, much effort is directed towards their improvement by rational structural changes. Most of useful anthracycline antibiotics chemistry is done by dissconnectionmodification approach, followed by de novo glycosidic bond assembly. It is pointed out that 1,2- and 2,3-unsaturated pyranosides constitute an important class of intermediates, useful for synthesis of natural and modified antibiotic aminosugars. Glycals derived from 3-amino-2,3,6-trideoxypyranoses and their 1-O-silylated derivatives are useful glycosyl donors for a variety of alcohols. Also anthracycline antibiotics can be obtained from them in simple preparative procedures which are amenable for scale up and technical process development. Moreover, unsaturated pyranoses from 6-deoxy-L-configurational series are useful chiral precursors for anthracycline aglycons synthesis. Remarkably, various synthetic schemes comprising anthracycline antibiotic sugars, aglycons and new synthetic analogues can be traced down to the single common precursor: 3,4-di-O-acetyl-L-rhamnal, easily obtained from a commodity chemical (raw material in food industry) L-rhamnose.

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    Tytuł oryginału: Glikozylacja z zastosowaniem pochodnych 1-tiocukrów jako substratów.
    Tytuł angielski: Derivatives of 1-thiosugars as substrates in glycosylation reactions.
    Autorzy: Szeja Wiesław, Bugla Joanna, Niemiec Aleksandra, Pastuch Gabriela, Kasprzycka Anna, Ślusarczyk Anna, Wandzik Ilona, Bieg Tadeusz, Przybysz Bogdan, Bogusiak Jadwiga
    Źródło: Wiad. Chem. 2002: 56 (7/8) s.605-625, il., sum.
    Sygnatura GBL: 310,575

    Hasła klasyfikacyjne GBL:
  • farmacja

    Streszczenie angielskie: It was found that carbohydrate parts 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 rapid development. The present paper gives an overview of development of 1-thiosugar derivatives in oligosaccharide syntesis. In the first part of this review, recent results of the use of thioglycosides, dithocarbonates, dithiocarbamates and thiophosphatase 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' glycosal donor, 'latent-active' glycosylation, orthogonal strategy are illustrated on several examples. The last part is devoted to methods for solid support oligosaccharide synthesis.

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