A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus

Jordi Alsina, T. Scott Yokum, Fernando Albericio, George Barany

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

A new variation of the Backbone Amide Linker (BAL) approach has been developed for N(α)-Fmoc solid-phase synthesis (SPS) of C-terminal modified peptides; this provides a convenient route to peptides containing prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. To illustrate the principles, several model peptides were prepared in high yields and excellent purities; diketopiperazines and racemized byproducts which otherwise form when alternative procedures are used were absent from the syntheses reported herein. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)7277-7280
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number38
DOIs
StatePublished - Sep 16 2000

Keywords

  • Backbone amide linker
  • C-terminal modified peptides
  • Diketopiperazines
  • Histidine
  • Proline
  • PyBOP
  • Racemization

Fingerprint Dive into the research topics of 'A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus'. Together they form a unique fingerprint.

Cite this