High-yielding Staudinger ligation of a phosphinothioester and azide to form a peptide.
[figure: see text] The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal alpha-azido group to form a single peptide that contains no residual atoms. Here diphenylphosphinomethanethiol thioesters are shown to give high isolated yields for this transformation. This finding provides precedent for a powerful and versatile new method for the total synthesis of proteins.
Nilsson
B L
BL
Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Kiessling
L L
LL
Raines
R T
RT
D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D011506:Proteins / Q000138:chemical synthesis*
D001386:Azides; D009946:Organothiophosphorus Compounds; D011506:Proteins