About: Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Synthetic routes for the preparation of new sugar nitriles 8-10 derived from 2-acetamido-2-deoxy-beta-D-glucopyranosides bearing a cyano group at the C-5 or C-6 position are presented. In an attempt to prepare the glycosyl azide 10 by treatment of tosylate 23 with KCN/DMF at 60 degrees C, an intramolecular 1,3-dipolar cycloaddition reaction occurred to give the highly constrained nonisolable tetrazole 24, which was readily converted into the imino-azido compound 25 through an azido-tetrazole tautomerism. Compounds 8 and 10 were found to be poorer substrates of fungal beta-N-acetylhexosaminidases than compound 9 and none of these compounds was accepted as substrates of the nitrilase or nitrile hydratase Synthetic routes for the preparation of new sugar nitriles 8-10 derived from 2-acetamido-2-deoxy-beta-D-glucopyranosides bearing a cyano group at the C-5 or C-6 position are presented. In an attempt to prepare the glycosyl azide 10 by treatment of tosylate 23 with KCN/DMF at 60 degrees C, an intramolecular 1,3-dipolar cycloaddition reaction occurred to give the highly constrained nonisolable tetrazole 24, which was readily converted into the imino-azido compound 25 through an azido-tetrazole tautomerism. Compounds 8 and 10 were found to be poorer substrates of fungal beta-N-acetylhexosaminidases than compound 9 and none of these compounds was accepted as substrates of the nitrilase or nitrile hydratase (en) Jsou představeny možnosti syntézy nových cukerných nitrilů 8-10 odvozených z 2-acetamido-2-deoxy-beta-D-glukopyranosidu, nesoucích kyanoskupinu v poloze C-5 nebo C-6. Ve snaze připravit glykosylazid 10 reakcí tosylátu s KCN/DMF při 60 °C došlo k intramolekulární 1,3-dipolární cykloadici za vzniku tetrazolu 24, který se bez možnosti izolace okamžitě přeměnil do azidu s iminoskupinou 25, svého tautomeru. Sloučeniny 8 a 10 byly horšími substráty beta-N-acetylhexosaminidas než sloučenina 9 a žádná z těchto sloučenin nebyla substrátem nitrilasy ani nitrilhydratasy (cs)
Title	Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions (en) Kyanodeoxyglykosylové deriváty jako substráty pro enzymatické reakce (cs)
skos:prefLabel	Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions (en) Kyanodeoxyglykosylové deriváty jako substráty pro enzymatické reakce (cs)
skos:notation	RIV/61388971:_____/06:00047992!RIV07-GA0-61388971
http://linked.open.../vavai/riv/strany	1876;1885
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/05/0172), P(GA203/05/2267), P(OC D25.001), P(OC D25.002), Z(AV0Z50200510), Z(AV0Z60870520), Z(MSM6007665808)
http://linked.open...iv/cisloPeriodika	-
http://linked.open...vai/riv/dodaniDat	2007
http://linked.open...aciTvurceVysledku	Martínková, Ludmila Bojarová, Pavla Křen, Vladimír
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Mikrobiologický ústav AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	470219
http://linked.open...ai/riv/idVysledku	RIV/61388971:_____/06:00047992
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	sugar nitriles; azido-tetrazole tautomerism; glycosidase (en)
http://linked.open.../riv/klicoveSlovo	glycosidase azido-tetrazole tautomerism sugar nitriles
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[654D0C797DCB]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	EE
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	http://linked.opendata.cz/resource/domain/vavai/projekt/OC%20D25.002 a-N-Acetylgalactosaminidase and a-galactosidase-structural and functional characterisation, use in synthesis of biologically important glycoconjugates Enzymes catalyzing stereoselective transformations of C-N bonds in organic compounds and the use of these biocatalysts to prepare chiral synthons http://linked.opendata.cz/resource/domain/vavai/projekt/OC%20D25.001
http://linked.open...UplatneniVysledku	2006
http://linked.open...v/svazekPeriodika	8
http://linked.open...iv/tvurceVysledku	Bojarová, Pavla Ettrich, Rüdiger Křen, Vladimír Martínková, Ludmila González, C. Carmona, A. T. Robina, I. Moreno-Vargas, A. J.
http://linked.open...n/vavai/riv/zamer	Microorganisms in Research and Biotechnology Spatial and functional dynamics of biological, ecological and socio-economic systems interacting with global climatic change Fyzikální biologie -nové přístupy v biologickém výzkumu
issn	1434-193X
number of pages	10 (xsd:int)
is http://linked.open...avai/riv/vysledek of	Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions Cyanodeoxy-Glycosyl Derivatives as Substrates for Enzymatic Reactions

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