Isoselenocyanates derived from amino acid esters: an expedient synthesis and application to the assembly of selenoureidopeptidomimetics, unsymmetrical selenoureas and selenohydantoins.
An important class of organoselenium compounds-α-isoselenocyanato esters 4 has been prepared by a reaction of α-isocyano esters with elemental selenium powder. The reaction issimple, rapid and all the isoselenocyanates have been isolated as stable ones after chromatographic purification. These hitherto unreported classes of molecules would be useful building blocks for the preparation of variety of selenium containing peptidomimetics. In this study, the utility of the title molecules in the preparation of selenoureidopeptidomimetics 6, unsymmetrical selenoureas 8 and selenohydantoins 10 is demonstrated.
Hemantha
Hosahalli P
HP
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr B. R. Ambedkar Veedhi, Bangalore-560 001, India.
Sureshbabu
Vommina V
VV
D000596:Amino Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006827:Hydantoins / Q000138:chemical synthesis*; D017953:Isocyanates / Q000737:chemistry; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D057786:Peptidomimetics / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000596:Amino Acids; D004952:Esters; D006827:Hydantoins; D017953:Isocyanates; D016566:Organoselenium Compounds; D057786:Peptidomimetics; D014508:Urea