Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

Boc-SPPS: Compatible linker for the synthesis of peptide o-aminoanilides

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

authors

  • Weidmann, J.
  • Dimitrijevic, E.
  • Hoheisel, J. D.
  • Dawson, Philip

publication date

  • 2016

journal

  • Organic Letters  Journal

abstract

  • A protection strategy is described for the efficient synthesis of peptide o-aminoanilides using in situ neutralization protocols for Boc-SPPS. On-resin protection of Boc-protected aminoacyl o-aminoanilides is achieved with 2-chlorobenzyl chloroformate. Activation through a peptidyl-benzotriazole intermediate allows for facile conversion to peptide-thioesters for use in native chemical ligation. In addition to providing a robust alternative to established thioester resins, as a latent thioester, the peptide o-aminoanilide has broad utility in convergent ligation strategies.

subject areas

  • Anilides
  • Biotin
  • Esters
  • Hepcidins
  • Molecular Structure
  • Peptides
scroll to property group menus

Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.5b03111

PubMed ID

  • 26702477
scroll to property group menus

Additional Document Info

start page

  • 164

end page

  • 167

volume

  • 18

issue

  • 2

©2019 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support