Synthetic circularized analogues of bovine pancreatic trypsin inhibitor

Judit Tulla-Puche, Irina V. Getun, Jordi Alsina, Fernando Albericio, George Barany

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Two cyclic analogues of the protein bovine pancreatic trypsin inhibitor (BPTI), c-[R]Smc and c-Cys5[R]Abu, have been synthesized. For the first target, a semisynthetic approach featured a cyclization that took advantage of the constraint imposed by the three disulfides of the native protein. For the second target, an entirely unstructured 58-residue thiolester, prepared by total synthesis with mild Fmoc chemistry and a side-chain anchoring strategy, was cyclized by native chemical ligation.

Original languageEnglish (US)
Pages (from-to)4541-4544
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number22
DOIs
StatePublished - Nov 12 2004

Keywords

  • Circular proteins
  • Cyclization
  • Native chemical ligation
  • Orthogonal protecting groups
  • Solid-phase synthesis
  • Thiolesters

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