4-alkoxy-2-hydroxybenzaldehyde (AHB): A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics

Toru Okayama, Andrew Burritt, Victor J. Hruby

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

(Formula presented) A new and versatile 4-alkoxy-2-hydroxybenzaldehyde (AHB) linker for solid-phase syntheses is described. Acylation of the polymer-bound secondary amine obtained from reductive amination of the aldehyde in the AHB linker showed good reactivity. Following acylation of the phenolic hydroxyl group, the resulting carboxamide resin was stable to treatment with 95% TFA. The O-acyl functional group was removed with 20% piperidine and the desired compound was cleaved from the resin by TFA treatment.

Original languageEnglish (US)
Pages (from-to)1787-1790
Number of pages4
JournalOrganic Letters
Volume2
Issue number13
DOIs
StatePublished - Jun 29 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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