✦ LIBER ✦

Mechanistic studies of amide bond scission during acidolytic deprotection of Pip containing peptide

✍ Scribed by Chiara Rubini; Alessio Osler; Andrea Calderan; Andrea Guiotto; Paolo Ruzza

Book ID: 105359668
Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 257 KB
Volume: 14
Category: Article
ISSN: 1075-2617
DOI: 10.1002/psc.1032

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Unusual TFA catalyzed cleavage reaction is reported for peptide containing pipecolic acid residues. Although the use of TFA under standard cleavage conditions is sufficiently mild to prevent degradation of the desired products, the amide bond between consecutive pipecolic acid residues is unexpectedly hydrolyzed by standard TFA treatment. The hydrolysis is proposed to proceed via an oxazolinium ion intermediate. This mechanism is supported by H/D exchange as observed by ESI‐MS and NMR experiments. Copyright © 2008 European Peptide Society and John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

Mechanistic Studies of an Unusual Amide

Mechanistic Studies of an Unusual Amide Bond Scission

✍ Creighton, Christopher J.; Romoff, Todd T.; Bu, Jane H.; Goodman, Murray 📂 Article 📅 1999 🏛 American Chemical Society 🌐 English ⚖ 173 KB

Studies on intramolecular hydrogen bondi

Studies on intramolecular hydrogen bonding between the pyridine nitrogen and the amide hydrogen of the peptide: synthesis and conformational analysis of tripeptides containing novel amino acids with a pyridine ring

✍ Masayuki Hanyu; Daisuke Ninomiya; Ryoji Yanagihara; Takashi Murashima; Toshifumi 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 203 KB

For the first time tripeptides, Z-AA(1)-Xaa-AA(3)-OMe (AA(1) and AA(3) = Gly or Aib, Xaa = 2Pmg and 2Pyg) were prepared containing alpha-methyl-alpha-(2-pyridyl)glycine (2Pmg) and alpha-(2-pyridyl)glycine (2Pyg) by solid-phase Ugi reaction. These results clearly indicate that for the preparation of