Bicyclic homodetic peptide libraries: comparison of synthetic strategies for their solid-phase synthesis.
Preliminary studies and synthesis development for the preparation of a bicyclic homodetic peptide library have been carried out using orthogonal protection schemes. The best results have been obtained using two Fmoc/tBu-based strategies, in which the first cycle is carried out in the solid phase through side chain functional groups previously protected with Aloc/Al groups. The second cycle is performed either in the solid phase, which requires side chain anchoring of a trifunctional amino acid and Dmb protection for the C-terminus carboxyl group, or in solution, which requires the use of highly labile resins, such as the 2-chlorotrityl (Barlos) resin. Only when the cycles are formed in a ziplike manner, that is, first the small cycle and then the larger ring, is the desired final product obtained.
Teixido
Meritxell
M
Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.
Altamura
Maria
M
Quartara
Laura
L
Giolitti
Alessandro
A
Maggi
Carlo Alberto
CA
Giralt
Ernest
E
Albericio
Fernando
F
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D019151:Peptide Library; D013678:Technology, Pharmaceutical / Q000379:methods*
D001643:Bridged Bicyclo Compounds; D019151:Peptide Library