Solid-phase synthesis of phenylalanine containing peptides using a traceless triazene linker.
J Org Chem
; 77(21): 9852-8, 2012 Nov 02.
Article
in En
| MEDLINE
| ID: mdl-23020637
ABSTRACT
The use of a triazene function to anchor phenylalanine to a polymeric support through its side chain is reported. To prove the usefulness of this strategy in solid-phase peptide synthesis, several bioactive peptides have been prepared including cyclic, C-modified, and protected peptides. The triazene linkage is formed by coupling the diazonium salt of Fmoc-Phe(pNH(2))-OAllyl to a MBHA-polystyrene resin previously functionalized with isonipecotic acid (90%). Further assembly of the peptide chain, cleavage from the resin using 2-5% TFA in DCM, and reduction of the resulting diazonium salt of the peptide with FeSO(4)·7H(2)O in DMF afforded the desired products in high purities (73-94%).
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Phenylalanine
/
Triazines
/
Solid-Phase Synthesis Techniques
Language:
En
Journal:
J Org Chem
Year:
2012
Type:
Article
Affiliation country:
Spain