320341-87-5Relevant academic research and scientific papers
Fluorescent and Nonfluorescent Aryl Vinyl Sulfones - Reagents Suitable for Protection and Detection of Thiol Functions
Horner, Leopold,Lindel, Hans
, p. 22 - 33 (2007/10/02)
The rate of the addition of primary, secondary, and tertiary thiols to aryl/alkyl vinyl sulfones 1 and 4-7 is investigated by competing reactions and by kinetics.The obtained acid stable 2-(alkyl-/arylthio)ethyl sulfones are cleaved by bases to give the starting material by rates corresponding to the rates of addition.Therefore, selective introduction and selective elimination of different (arylsulfonyl)ethyl protective groups in the same molecule is possible by using different kinetic steering factors. - Application of the fluorescent vinyl sulfones 5, 10, and 11 opens new fields for analysis and synthesis.SH-selective vinyl sulfones and thiophosphinic acid cyanides are "orthogonal" protective groups.
ARYL VINYL SULFONES AS THIOL PROTECTIVE GROUP
Kuroki, Yoshiaki,Lett, Robert
, p. 197 - 200 (2007/10/02)
Phenyl vinyl sulfone and p-tolyl isobutenyl sulfone are convenient reagents for protecting SH groups via the Michael adduct.Protection and deprotection can be achieved in high yields under mild basic conditions, in protic or aprotic solvents.
ARYL-VINYLSULFONE--REAGENTIEN ZUM SCHUTZ UND NACHWEIS VON THIOLFUNKTIONEN
Horner, L.,Lindel, H.
, p. 1 - 8 (2007/10/02)
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.
