Traceless Staudinger ligation reagent with borane protecting group.
The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.[1]
After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.[2]
The Journal of organic chemistry, 67(14), 4993-4996 (2002-07-06)
The Staudinger ligation of peptides with a C-terminal phosphinothioester and N-terminal azide is an emerging method in protein chemistry. Here, the first Staudinger ligations of nonglycyl azides are reported and shown to proceed both in nearly quantitative yield and with
The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the