Use of trichloroacetimidate linker in solid-phase Peptide synthesis.
A solid-phase method for the preparation of C-terminal amino-alcohol-containing peptides using activated Wang resin is presented. A diverse set of (fluorenylmethoxy)carbonyl (Fmoc) protected amino alcohols was found to load rapidly and efficiently. The synthetic utility of this approach was demonstrated through the direct synthesis of the peptide drug octreotide with excellent yield and purity. These results suggest that the use of trichloroacetimidate activated resins offers an attractive alternative in the preparation of this class of peptides.
Yan
Liang Zeng
LZ
Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, USA.
Mayer
John P
JP
D000081:Acetamides; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D062845:Chloroacetates; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D015394:Molecular Structure; D015282:Octreotide / Q000138:chemical synthesis*; D010455:Peptides / Q000032:analysis / Q000138:chemical synthesis*
D000081:Acetamides; D062845:Chloroacetates; D007202:Indicators and Reagents; D010455:Peptides; C009528:trichloroacetamide; D015282:Octreotide