Synthesis of side-chain to side-chain cyclic peptides and oligolysine cores suitable for the solid-phase assembly of MAPs and TASPs.

Aletras A; Barlos K; Gatos D; Koutsogianni S; Mamos P

International Journal of Peptide and Protein Research 1995; 45(5): 488-96.

Abstract: The Nε-Mtt function of Nα-9-Fluorenylmethoxycarbonyl-Nε-4-methyltrityl-lysine, [Fmoc-Lys(Mtt)-OH] can be quantitatively removed upon treatment with 1% TFA in dichloromethane or with a 1:2:7 mixture of acetic acid –trifluoroethanol-dichloromethane for 30 min and 1 h at room temperature, respectively. Under these conditions, groups of the tert-butyl type and peptide ester bonds to TFA-labile resins, such as the 2-chlorodiphenylmethyl- and the Wang-resin, remained intact. The utility of the new derivative in peptide synthesis has been exemplified with the synthesis of a cyclic cholecystokinin analog. As an example of further application, five types of lysine cores suitable for the solid-phase synthesis of one, two or three epitopes containing antigenic peptides or template-assembled synthetic proteins have been synthesized on Merrifield, Wang and 2-chlorodiphenylmethyl resin.

Categories: Knowledge Base Amino Acids