91271-26-0Relevant articles and documents
Organophosphorus Compounds, 111. Phosphinic and Thiophosphinic Cyanides as Fluorescent SH-selective Reagents
Horner, Leopold,Lindel, Hans
, p. 676 - 682 (2007/10/02)
The fluorescent thiophosphinic cyanides 7 and 8 are SH-selective, the corresponding thiophosphinic chlorides 5 and 6 are in general NH2-selective (exception: the methyl ester of cysteine is S-thiophosphinoylated).The fluorescent dithiophosphinic esters, for example 11 - 14, obtained in this way, are of analytical value.The SH-compounds are regenerated by fluorolysis of the dithiophosphinic esters.Diphenylthiophosphinic cyanide is more suitable for the application in synthesis than the compounds 7 and 8.
PHOSPHORORGANISCHE VERBINDUNGEN 108. DIE SYNTHESE FLUORESZIERENDER UND CHEMOSELEKTIVER REAGENTIEN ZUM GEZIELTEN NACHWEIS UND SCHUTZ BIOLOGISCH WICHTIGER FUNKTIONELLER GRUPPEN
Horner, Leopold,Flemming, Hans-Wolfram
, p. 345 - 362 (2007/10/02)
Compounds of type A are fluorescent, if the donator groups, like NMe2, OMe, SMe and PR2, and the acceptor groups, like R'P(O)X, SO2R' and CO2R', are linked to different nuclei of the naphthalin ring system.The chemoselectivity of the electrophilic phosphoryl compounds P(O)X to nucleophiles like ROH, RNHR' and RSH is determined by the nature of the leaving group X responsible for different reaction mechanism.Phosphoryl groups with X = Cl attack predominantly R-NHR'- groups; phosphoryl compounds with X = F and OC6H4NO2(p) are ROH-selective.In this publication compounds of type A are presented, in which fluorescence and chemoselectivity are combined by structure in one molecule.These compounds are important analytic reagents (prove of the functional groups in the active site of enzymes) and as protective groups in the synthesis of natural products like peptides.
