Stability of 5(6)-Carboxyfluorescein
in Microwave-Assisted Synthesis of Fluorescein-Labelled
O-Dimannosylated Peptides

Renata Kowalczyk; Paul W. R. Harris; Rod P. Dunbar; Margaret A. Brimble

doi:10.1055/s-0029-1216820

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Synthesis 2009(13): 2210-2222
DOI: 10.1055/s-0029-1216820

PAPER

Stability of 5(6)-Carboxyfluorescein in Microwave-Assisted Synthesis of Fluorescein-Labelled O-Dimannosylated Peptides

Renata Kowalczyk^a,c, Paul W. R. Harris^a,c, Rod P. Dunbar^b,c, Margaret A. Brimble*^a,c
^a Department of Chemistry, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand
^b School of Biological Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand
^c Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Further Information

Publication History

Received 11 February 2009
Publication Date:
14 May 2009 (online)

Abstract
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Abstract

Methodology for the efficient, automated and microwave-assisted Fmoc solid-phase synthesis of a 5(6)-carboxyfluorescein-labelled Lys(Dde)-Gly-Wang resin that can be further elongated through the lysine N ^ε amino group is described. Incorporation of O-dimannosylated peptides onto this resin using Fmoc-[α-d-Man(OBz)₄-(1→6)-α-d-Man(OBz)₃α1-]Ser-OH and PEG-[α-d-Man(OBz)₄-(1→6)-α-d-Man(OBz)₃α1-]-OH building blocks is demonstrated. Conditions were optimised to enable the efficient automated synthesis of several carboxyfluorescein-labelled dimannosylated peptides. 5(6)-Carboxyfluorescein was shown to be stable to the microwave conditions used for glycopeptide synthesis. The methodology described provides a robust, flexible synthetic platform for the preparation of a variety of fluorescently labelled glycopeptides (especially O-dimannosylated peptides) for biological evaluation.

Key words

carbohydrates - glycopeptides - mannosylated amino acids - glycosylations - solid-phase synthesis

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