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Application of the trimethylsilyl trifluoromethanesulfonate deprotecting procedure for the synthesis of porcine peptide YY (PYY) |
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| Authors: | SEISHI ONO SHINYA KIYAMA KOUKI KITAGAWA SHIROH FUTAKI TOMOHIKO NAKAMURA TAKASHI TAIKE TADASHI AKITA SHOICHIRO SUMI KAZUTOMO INOUE MASAKI FUJIMURA TAKAYOSHI TOBE HARUAKI YAJIMA |
| Abstract: | A 36-residue peptide amide corresponding to the entire amino acid sequence of porcine peptide YY (PYY) was synthesized by assembling eight peptide fragments of established purity, followed by hard acid deprotection with 1m trimethylsilyl trifluoromethanesulfonate in trifluoroacetic acid. β-Cycloheptylaspartate, Asp(OChp), was employed to minimize the base-catalyzed succinimide formation. When administered to dogs, synthetic PYY was active as natural peptide in its effects on exocrine pancreatic secretion and pancreatic tissue blood flow. |
| Keywords: | base-catalyzed succinimide formation β -cycloheptylaspartate hard acid deprotection porcine peptide YY (PYY) synthesis thioanisole-mediated deprotection trifluoromethanesulfonic acid deprotection trimethylsilyl trifluoromethanesulfonate deprotection |