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

Christian A Olsen; Malene 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

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

10 Citations (Scopus)

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.

Original language	English
Journal	Organic Letters
Volume	7
Issue number	9
Pages (from-to)	1703-6
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol050305o
Publication status	Published - 2005

Keywords

Combinatorial Chemistry Techniques
Fluorobenzenes
Models, Molecular
Molecular Structure
Oligopeptides
Spider Venoms
Tyrosine
Wasp Venoms

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10.1021/ol050305o

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

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.",

keywords = "Combinatorial Chemistry Techniques, Fluorobenzenes, Models, Molecular, Molecular Structure, Oligopeptides, Spider Venoms, Tyrosine, Wasp Venoms",

author = "Olsen, {Christian A} and Malene J{\o}rgensen and Hansen, {Steen H} and Matthias Witt and Jaroszewski, {Jerzy W} and Henrik Franzyk",

year = "2005",

doi = "10.1021/ol050305o",

language = "English",

volume = "7",

pages = "1703--6",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Side-chain-anchored N(alpha)-Fmoc-Tyr-OPfp for bidirectional solid-phase synthesis

AU - Olsen, Christian A

AU - Jørgensen, Malene

AU - Hansen, Steen H

AU - Witt, Matthias

AU - Jaroszewski, Jerzy W

AU - Franzyk, Henrik

PY - 2005

Y1 - 2005

N2 - [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.

AB - [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.

KW - Combinatorial Chemistry Techniques

KW - Fluorobenzenes

KW - Models, Molecular

KW - Molecular Structure

KW - Oligopeptides

KW - Spider Venoms

KW - Tyrosine

KW - Wasp Venoms

U2 - 10.1021/ol050305o

DO - 10.1021/ol050305o

M3 - Journal article

C2 - 15844885

SN - 1523-7060

VL - 7

SP - 1703

EP - 1706

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

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

Abstract

Keywords

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