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DOI: 10.1055/s-0029-1216820
Stability of 5(6)-Carboxyfluorescein in Microwave-Assisted Synthesis of Fluorescein-Labelled O-Dimannosylated Peptides
Publication History
Publication Date:
14 May 2009 (online)
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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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