Caged O-phosphorothioyl amino acids as building blocks for Fmoc-based solid phase peptide synthesis.
The synthesis of 1-(2-nitrophenylethyl) caged O-phosphorothioylserine, -threonine and -tyrosine derivatives is reported. These amino acid building blocks can be directly incorporated into peptides by Fmoc-based solid phase synthesis as their pentafluorophenyl esters or as symmetric anhydrides. Upon irradiation with UV light, the thiophosphate group, representing a hydrolysis resistant phosphate analog, is revealed.
Aemissegger
Andreas
A
Massachusetts Institute of Technology, Department of Chemistry, 18-590, 77 Massachusetts Ave., Cambridge, MA 02139, USA.
Carrigan
Christina N
CN
Imperiali
Barbara
B