Your browser version may not work well with NCBI's Web applications. More information here...
1: J Comb Chem. 2003 Nov-Dec;5(6):760-8.Click here to read Links

Bicyclic homodetic peptide libraries: comparison of synthetic strategies for their solid-phase synthesis.

Teixido M, Altamura M, Quartara L, Giolitti A, Maggi CA, Giralt E, Albericio F.

Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.

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.

PMID: 14606803 [PubMed - indexed for MEDLINE]