Very efficient Coupling reagent used for solid and solution phase peptide synthesis. Compatible with both Boc and Fmoc chemistries. Coupling reactions are complete in as little as six minutes and when HOBt is added and racemization can be reduced to insignificant levels. 1 TBTU is very effective, for instance, in key macrocyclization and coupling steps in the total synthesis of the macrocyclic peptide cyclotheonamide B.2 Excess TBTU can react with the unprotected N-terminal of the peptide and form a guanylidine moiety that blocks further elongation of the peptide. TBTU has been used as an activating agent of carboxylic acids for preparation of 1,2,4, oxadiazoles, amides and phenylhydrazides, and esters.3, 4, 5
1. Tetrahedron Lett. 1989, 30, 1927.
2. J. Org. Chem. 1997, 62, 3880.
3. Tetrahedron Lett. 2001, 42, 1495.
4. Chin. J.Chem. 2008, 26, 1141.
5. ARKIVOC. 2007, 13, 47.