Side-chain-anchored N(alpha)-Fmoc-Tyr-OPfp for bidirectional solid-phase synthesis.
[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.
Olsen
Christian A
CA
Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
Jørgensen
Malene R
MR
Hansen
Steen H
SH
Witt
Matthias
M
Jaroszewski
Jerzy W
JW
Franzyk
Henrik
H
D020650:Combinatorial Chemistry Techniques; D005464:Fluorobenzenes / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis*; D013111:Spider Venoms / Q000138:chemical synthesis*; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014862:Wasp Venoms / Q000138:chemical synthesis*
D005464:Fluorobenzenes; C507452:N(alpha)-Fmoc-Tyr-OPfp; D009842:Oligopeptides; D013111:Spider Venoms; D014862:Wasp Venoms; D014443:Tyrosine