Search results for "Vinyl sulfone"
showing 10 items of 14 documents
ChemInform Abstract: Diels-Alder Reactions of in situ Generated N-Benzoylindolo-2,3- quinodimethane with Carbodienophiles.
2010
The indolo-2,3-quinodimethane (5), generated from 2,3-bis(bromomethyl)indole (4), was trapped with unsymmetrical carbodienophiles or N, N′-p-phenylenedimaleimide to furnish the 1,2,3,4-tetrahydrocarbazoles (6–9). [4 + 2]-Cycloaddition of 5 with tetracyanoethylene gave rise to the tetracyanocarbazole (10) and a subsequent product 11a or 11b. The Diels-Alder reaction of 5 with divinyl sulfone was regiospecific within the detection limits of HPLC analysis. Similarly, the reaction of 5 with N, N′-p-phenylenedimaleimide yielded solely the stereoisomer 9.
Self-adjuvanting C18 lipid vinil sulfone-PP2A vaccine: study of the induced immunomodulation against Trichuris muris infection
2017
Despite the importance of the adjuvant in the immunization process, very few adjuvants merge with the antigens in vaccines. A synthetic self-adjuvant oleic-vinyl sulfone (OVS) linked to the catalytic region of recombinant serine/threonine phosphatase 2A from the nematode Angiostrongylus costaricensis (rPP2A) was used for intranasal immunization in mice previously infected with Trichuris muris . The animal intranasal immunization with rPP2A-OVS showed a reduction of 99.01% in the number of the nematode eggs and 97.90% in adult. The immunohistochemical analysis of the intestinal sections showed that in immunized animals with lipopeptide the mucus was significantly higher than in the other ex…
Copper-catalyzed regioselective synthesis of (E)-β-fluorovinyl sulfones
2019
Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed (E)-&beta
Potentialgesteuerte SS-Bindungsspaltung und Fluoreszenzmarkierungsstudien am Beispiel des Rinderinsulins
1985
Die drei SS-Brucken im Insulin konnen galvanostatisch unter Bildung der SH-A-Kette und der SH-B-Kette (Produktgemisch I) aufgespalten werden. Potentiostatisch gelingt bei -1.3 V (vs. SCE) die selektive Offnung der zwei interchenaren Disulfidbrucken (Produktgemisch II). Die vier SH-Gruppen im Produktgemisch II werden mit dem Vinylsulfon 1 blockiert (Produktgemisch III). Im Produktgemisch III wird die intrachenare Disulfidbrucke in der teilblockierten A-Kette bei -1.8 V (vs. SCE) potentiostatisch reduktiv geoffnet und mit dem fluoreszierenden Arylvinylsulfon 2 geschutzt (Produktgemisch IV). Auch die SH-Gruppen in den Produktgemischen I und II werden durch die fluoreszierenden Vinylsulfone 2 u…
Phosphororganische Verbindungen, 113. Chemoselektive gesteuerte Fluoreszenzmarkierung von α-Chymotrypsin
1985
α-Chymotrypsin wird durch die fluoreszierenden Phosphonoylfluoride 1 und 3 inhibiert. Die fluoreszenzmarkierten α-Chymotrypsine 5 und 6 wurden gelelektrophoretisch aufgetrennt. Die Fluoreszenz von 1 und 3 sowie 5 und 6 ist komplementar losungsmittelabhangig. Mit 3 fluoreszenzmarkiertes α-Chymotrypsin ergibt bei der sauren Hydrolyse den fluoreszierenden Serinester 7. Durch reduktive Offnung der SS-Brucken im fluoreszenzmarkierten 6 wird bewiesen, das 1 mit einem Serin der C-Kette reagiert hat. Das gleiche Ergebnis erhalt man, wenn man in 6 die durch Reduktion freigesetzten SH-Gruppen zunachst mit Vinylsulfonen blockiert und dann auftrennt. Organophosphorus Compounds, 113. — Chemoselectively …
ARYL-VINYLSULFONE—REAGENTIEN ZUM SCHUTZ UND NACHWEIS VON THIOLFUNKTIONEN
1983
Abstract Aryl vinyl sulfones selectively react with thiol groups to acid-stable compounds which easily are cleaved by mild bases to thiol compounds. Ester and amide groups are not attacked under these conditions. Therefore, these compounds are good protecting groups or labels in peptide chemistry. The following aryl vinyl sulfones were investigated: phenyl vinyl sulfone 1, p-carbethoxyphenyl vinyl sulfone 15 and the fluorescent 5-dimethylaminonaphthyl 1-vinyl sulfone 5 and 5-methoxynaphthyl-1 vinyl sulfone 10. The last two compounds are very useful reagents for the quantitative determination of SH-groups in polypeptides such as enzymes. Aryl-vinylsulfone reagieren selektiv mit Thiolgruppen …
Diels-Alder Reactions ofin situ generated N-benzoylindolo-2,3-quinodimethane with carbodienophiles
1993
The indolo-2,3-quinodimethane (5), generated from 2,3-bis(bromomethyl)indole (4), was trapped with unsymmetrical carbodienophiles or N, N′-p-phenylenedimaleimide to furnish the 1,2,3,4-tetrahydrocarbazoles (6–9). [4 + 2]-Cycloaddition of 5 with tetracyanoethylene gave rise to the tetracyanocarbazole (10) and a subsequent product 11a or 11b. The Diels-Alder reaction of 5 with divinyl sulfone was regiospecific within the detection limits of HPLC analysis. Similarly, the reaction of 5 with N, N′-p-phenylenedimaleimide yielded solely the stereoisomer 9.
Chemoselektive Fluoreszenzstudien am Subtilisin und “Thiosubtilisin”
1985
Chemoselective Fluorescence Studies with Subtilisin and “Thiosubtilisin” The serine hydroxy group in the active site of subtilisin is selectively “phosphylated”3). This is demonstrated using the fluorescent phosphinic fluoride 1. “Thiosubtilisin” does not react with 1 but with the SH-selective and fluorescent vinyl sulfone 2.
Self-adjuvanting C18 lipid vinil sulfone-PP2A vaccine: study of the induced immunomodulation against
2017
Despite the importance of the adjuvant in the immunization process, very few adjuvants merge with the antigens in vaccines. A synthetic self-adjuvant oleic-vinyl sulfone (OVS) linked to the catalytic region of recombinant serine/threonine phosphatase 2A from the nematode Angiostrongylus costaricensis (rPP2A) was used for intranasal immunization in mice previously infected with Trichuris muris. The animal intranasal immunization with rPP2A-OVS showed a reduction of 99.01% in the number of the nematode eggs and 97.90% in adult. The immunohistochemical analysis of the intestinal sections showed that in immunized animals with lipopeptide the mucus was significantly higher than in the other expe…
Gezielte und reversible Fluoreszenzmarkierung von SH-Lysozym mit Vinylsulfonen
1985
Am Beispiel von SH-Lysozym wird gezeigt, wie man SH-Gruppen reversibel mit den Vinylsulfonen 1–4 nach Gl. (a) selektiv blockieren und nach Gl. (b) selektiv deblockieren kann. Das wasserlosliche Vinylsulfon 2 macht das blockierte SH-Lysozym wasserloslich. Durch Einwirkung von NaOH-Losung wird nach Gl. (b) das wasserunlosliche SH-Lysozym regeneriert. Die fluoreszierenden Vinylsulfone 3 und 4 konnen als Fluoreszenzmarker nach verschiedenen Arbeitsweisen zum qualitativen Nachweis und zur quantitativen Bestimmung von SH-Gruppen herangezogen werden. Selective and Reversible Fluorescence Marking of SH-Lysozyme with Vinyl Sulfones The SH groups of SH-lysozyme as a model substance are selectively bl…