Application of the trimethylsilyl trifluoromethanesulfonate deprotecting procedure for the synthesis of porcine peptide YY (PYY).
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. beta-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.
Ono
S
S
Faculty of Pharmaceutical Sciences, University of Tokushima, Japan.
Kiyama
S
S
Kitagawa
K
K
Futaki
S
S
Nakamura
T
T
Taike
T
T
Akita
T
T
Sumi
S
S
Inoue
K
K
Fujimura
M
M
D000595:Amino Acid Sequence; D000818:Animals; D008698:Mesylates; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000138:chemical synthesis; D019894:Peptide YY; D010455:Peptides / Q000138:chemical synthesis*; D013552:Swine; D014297:Trimethylsilyl Compounds
D008698:Mesylates; D010446:Peptide Fragments; D010455:Peptides; D014297:Trimethylsilyl Compounds; D019894:Peptide YY; C053353:trimethylsilyl trifluoromethanesulfonate