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Total solid‐phase synthesis of bombesin analogs with different functional groups at the C ‐terminus
Author(s) -
AbdElgaliel Wael R.,
Gallazzi Fabio,
Lever Susan Z.
Publication year - 2007
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.878
Subject(s) - chemistry , cleavage (geology) , peptide , hydroxymethyl , bombesin , residue (chemistry) , solid phase synthesis , benzoic acid , side chain , hydrazide , peptide synthesis , nucleophile , high performance liquid chromatography , amino acid , combinatorial chemistry , stereochemistry , chromatography , organic chemistry , biochemistry , catalysis , polymer , receptor , geotechnical engineering , neuropeptide , fracture (geology) , engineering
Five bombesin analogs with different functional groups at the C ‐terminus were synthesized using a solid‐phase strategy. The protocols were optimized using 4‐(hydroxymethyl)benzoic acid (HMBA) resin to synthesize a common precursor followed by nucleophilic cleavage of the base sensitive peptide ester linkage. The C ‐terminal modifications included ethylamide, butylamide, methyl ester, propyl ester and hydrazide. Cleavage from the resin was possible with the fully protected or deprotected precursor peptide; however, higher purity of the final products was achieved when cleavage protocols were conducted after side‐chain deprotection. The synthesized peptides were analyzed and characterized using reverse phase HPLC and ESI‐MS. The peptides were obtained in 13–32% overall recovery, calculated from the coupling efficiency of the first amino acid residue, and in 91–97% purity. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.