About: Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles

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About: Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles Goto Sponge NotDistinct Permalink

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Description	Five flavin (isoalloxazine) and alloxazine adducts with O-nucleophiles, 5-ethyl-4a-hydroxy-3,7,8,10-tetramethyl-4a,5-dihydroisoalloxazine (1a-OH), 5-ethyl-4a-hydroxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OH), 5-ethyl-4a-methoxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OMe), 5-ethyl-4a-hydroxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OH) and 5-ethyl-4a-methoxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OMe) were prepared from the corresponding salts, 5-ethyl-3,7,8,10-tetramethylisoalloxazinium (la), 5-ethyl-3,10-dimethylisoalloxazinium (1b) and 5-ethyl-1,3-dimethylalloxazinium (2a) perchlorates by the addition of a nucleophile (water or methanol) and triethylamine as a base. The prepared adducts represent artificial analogs of Flavin cofactor derivatives which are essential for the functioning of flavoenzymes. They were characterized by (1)H and (13)C NMR, HR-MS and UV-VIS spectra. In the cases of la-OH, 1b-OH, and 2a-OMe, the crystal structures were determined by X-ray diffraction. Flavinium and alloxazinium salts are in rapid equilibria with their adducts in water or methanolic solutions without the presence of a base. It was found that the equilibrium constants for flavin adduct formation is higher by six orders of magnitude than those for alloxazine derivatives. The presence of the sp(3) hybridized C4a atom in the molecule of the adducts causes deviation from planarity. The inter-planar angles between benzene and the pyrimidine ring were found to be 31.5 degrees, 23.64 degrees and 15.62 degrees for 1a-OH, 1b-OH and 2a-OMe, respectively, which are much higher than those of previously published adducts of C-nucleophiles. In isoalloxazine adducts, delocalization of pi electrons between the N10-C10a and C10a-N1 bonds was detected while the length of the N10-C10a and C10a-N1 bonds in the alloxazine adducts corresponds to a double and single bond, respectively. Five flavin (isoalloxazine) and alloxazine adducts with O-nucleophiles, 5-ethyl-4a-hydroxy-3,7,8,10-tetramethyl-4a,5-dihydroisoalloxazine (1a-OH), 5-ethyl-4a-hydroxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OH), 5-ethyl-4a-methoxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OMe), 5-ethyl-4a-hydroxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OH) and 5-ethyl-4a-methoxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OMe) were prepared from the corresponding salts, 5-ethyl-3,7,8,10-tetramethylisoalloxazinium (la), 5-ethyl-3,10-dimethylisoalloxazinium (1b) and 5-ethyl-1,3-dimethylalloxazinium (2a) perchlorates by the addition of a nucleophile (water or methanol) and triethylamine as a base. The prepared adducts represent artificial analogs of Flavin cofactor derivatives which are essential for the functioning of flavoenzymes. They were characterized by (1)H and (13)C NMR, HR-MS and UV-VIS spectra. In the cases of la-OH, 1b-OH, and 2a-OMe, the crystal structures were determined by X-ray diffraction. Flavinium and alloxazinium salts are in rapid equilibria with their adducts in water or methanolic solutions without the presence of a base. It was found that the equilibrium constants for flavin adduct formation is higher by six orders of magnitude than those for alloxazine derivatives. The presence of the sp(3) hybridized C4a atom in the molecule of the adducts causes deviation from planarity. The inter-planar angles between benzene and the pyrimidine ring were found to be 31.5 degrees, 23.64 degrees and 15.62 degrees for 1a-OH, 1b-OH and 2a-OMe, respectively, which are much higher than those of previously published adducts of C-nucleophiles. In isoalloxazine adducts, delocalization of pi electrons between the N10-C10a and C10a-N1 bonds was detected while the length of the N10-C10a and C10a-N1 bonds in the alloxazine adducts corresponds to a double and single bond, respectively. (en)
Title	Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles (en)
skos:prefLabel	Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles (en)
skos:notation	RIV/60461373:22810/11:43892807!RIV12-MSM-22810___
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/07/1246), Z(AV0Z40550506), Z(MSM6046137302)
http://linked.open...iv/cisloPeriodika	1-3
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Dvořáková, Hana
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	Vysoká škola chemicko-technologická v Praze / Rektorát
http://linked.open...dnocenehoVysledku	233887
http://linked.open...ai/riv/idVysledku	RIV/60461373:22810/11:43892807
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	SULFIDES; SALTS; OXYGEN; AMINES; H2O2 OXIDATIONS; ELECTRON-TRANSFER; CRYSTAL-STRUCTURES; MOLECULAR-STRUCTURE; HYDROGEN-PEROXIDE; MONOAMINE-OXIDASE CATALYSIS (en)
http://linked.open.../riv/klicoveSlovo	SALTS AMINES ELECTRON-TRANSFER H2O2 OXIDATIONS MOLECULAR-STRUCTURE MONOAMINE-OXIDASE CATALYSIS OXYGEN SULFIDES CRYSTAL-STRUCTURES HYDROGEN-PEROXIDE
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[7C8D95DEBFE6]
http://linked.open...i/riv/nazevZdroje	Journal of Molecular Structure
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Chiral flavinium salts as organocatalysts for enantioselective sulfoxidations and N-oxidations
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	1004
http://linked.open...iv/tvurceVysledku	Cibulka, Radek Dvořáková, Hana Šanda, Miloslav Ménová, Petra Eigner, Václav Čejka, Jan
http://linked.open...ain/vavai/riv/wos	000296927300024
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství Preparation and research of functional materials and material technologies using micro- and nanoscopic methods
issn	0022-2860
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.molstruc.2011.08.002
http://localhost/t...ganizacniJednotka	22810

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