Side-chain-anchored N(alpha)-Fmoc-Tyr-OPfp for bidirectional solid-phase synthesis

Christian A Olsen; Malene R Jørgensen; Steen H Hansen; Matthias Witt; Jerzy W Jaroszewski; Henrik Franzyk

doi:10.1021/ol050305o

Side-chain-anchored N(alpha)-Fmoc-Tyr-OPfp for bidirectional solid-phase synthesis

Org Lett. 2005 Apr 28;7(9):1703-6. doi: 10.1021/ol050305o.

Authors

Christian A Olsen¹, Malene R Jørgensen, Steen H Hansen, Matthias Witt, Jerzy W Jaroszewski, Henrik Franzyk

Affiliation

¹ Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, Universitetsparken 2, DK-2100 Copenhagen, Denmark.

PMID: 15844885
DOI: 10.1021/ol050305o

Abstract

[reaction: see text] A mild resin-immobilization strategy employing a readily prepared trityl bromide resin for anchoring building blocks via a phenol group has been developed. With N(alpha)-Fmoc-Tyr-OPfp as a starter building block, it was possible to prepare asymmetrically substituted hybrids of spider- and wasp-type polyamine toxins using solid-phase peptide synthesis conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Combinatorial Chemistry Techniques*
Fluorobenzenes / chemical synthesis*
Models, Molecular
Molecular Structure
Oligopeptides / chemical synthesis*
Spider Venoms / chemical synthesis*
Tyrosine / analogs & derivatives*
Tyrosine / chemical synthesis
Wasp Venoms / chemical synthesis*

Substances

Fluorobenzenes
N(alpha)-Fmoc-Tyr-OPfp
Oligopeptides
Spider Venoms
Wasp Venoms
Tyrosine