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  • Glycosyl azides are shown to be efficient donors for Alfa-galactosidases, Alfa-glucosidases and Alfa-mannosidases. Only Alfa-galactosidases do not cleave the respective glycosyl azide 1 and, moreover, they exhibit competitive inhibition (especially Alfa-galactosidase from Talaromyces flavus). High water solubility and ready synthesis of glycosyl azides enable transglycosylation reactions even with difficult acceptors like N-acetyl-D-mannosamine in good yields. The versatility of glycosyl azides was demonstrated in the synthesis of five disaccharides – two of them are described for the first time. All the reactions were highly regioselective, yielding isomers. Alfa-Galactosidase from E. coli proved to have the best synthetic capabilities. The present study shows that glycosyl azides are a valuable alternative to common p-nitrophenyl glycoside donors and in many synthetic reactions
  • Glycosyl azides are shown to be efficient donors for Alfa-galactosidases, Alfa-glucosidases and Alfa-mannosidases. Only Alfa-galactosidases do not cleave the respective glycosyl azide 1 and, moreover, they exhibit competitive inhibition (especially Alfa-galactosidase from Talaromyces flavus). High water solubility and ready synthesis of glycosyl azides enable transglycosylation reactions even with difficult acceptors like N-acetyl-D-mannosamine in good yields. The versatility of glycosyl azides was demonstrated in the synthesis of five disaccharides – two of them are described for the first time. All the reactions were highly regioselective, yielding isomers. Alfa-Galactosidase from E. coli proved to have the best synthetic capabilities. The present study shows that glycosyl azides are a valuable alternative to common p-nitrophenyl glycoside donors and in many synthetic reactions (en)
  • Práce ukazuje, že glykosylazidy jsou efektivní donory pro Alfa-galaktosidasy, Alfa-glukosidasy a Alfa-mannosidasy. Pouze Alfa-galaktosidasy neštěpí glykosylazid 1 a navíc vykazují kompetitivní inhibici (zvláště Alfa-galaktosidasa z Talaromyces flavus). Výborná rozpustnost ve vodě a jednoduchá syntéza glykosylazidů umožňují transglykosylační reakce s dobrými výtěžky i s problematickými akceptory jako N-acetyl-D-mannosamin. Všestrannost glykosylazidů byla demonstrována na syntéze pěti disacharidů, z nichž dva jsou popsány poprvé. Všechny reakce byly vysoce regioselektivní a vznikaly při nich isomery. Alfa-Galaktosidasa z E. coli měla nejlepší syntetické schopnosti. Tato studie ukazuje, že glykosylazidy jsou cennou alternativou běžně používaných p-nitrofenyl-glykosidových donorů v mnoha syntetických reakcích (cs)
Title
  • Glycosyl Azides – An Alternative Way to Disaccharides
  • Glycosyl Azides – An Alternative Way to Disaccharides (en)
  • Glykosyl azidy – alternativní cesta k disacharidům (cs)
skos:prefLabel
  • Glycosyl Azides – An Alternative Way to Disaccharides
  • Glycosyl Azides – An Alternative Way to Disaccharides (en)
  • Glykosyl azidy – alternativní cesta k disacharidům (cs)
skos:notation
  • RIV/61388971:_____/07:00097666!RIV08-AV0-61388971
http://linked.open.../vavai/riv/strany
  • 1514;1520
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(GA203/05/0172), P(IAA400200503), P(OC 136), P(OC 170), P(OC D25.001), V, Z(AV0Z50200510)
http://linked.open...iv/cisloPeriodika
  • 8-9
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 423503
http://linked.open...ai/riv/idVysledku
  • RIV/61388971:_____/07:00097666
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • azides; enzyme calatysis; glycosylation (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [E1DFD2F895BC]
http://linked.open...i/riv/nazevZdroje
  • Advanced Synthesis & Catalysis
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 349
http://linked.open...iv/tvurceVysledku
  • Bojarová, Pavla
  • Křen, Vladimír
  • Kuzma, Marek
  • Monti, D.
  • Pelantová, Helena
  • Petrásková, Lucie
  • Simerská, Pavla
  • Ferrandi, E. E.
http://linked.open...n/vavai/riv/zamer
issn
  • 1615-4150
number of pages
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