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

作者：Kowalczyk Renata; Harris Paul W R; Dunbar Rod P; Brimble Margaret A^*

来源：Synthesis, 2009, 2009(13): 2210-2222.

DOI：10.1055/s-0029-1216820

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

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(epsilon) amino group is described. Incorporation of O-dimannosylated peptides onto this resin using Fmoc-[alpha-D-Man(OBz)(4)-(1 -> 6) -alpha-D-Man(OBz)(3)alpha l-]Ser-OH and PEG-[alpha-D-Man(OBZ)(4)-(1 -> 6)-alpha-D-Man(OBz)(3)alpha l-]-OH building blocks is demonstrated. Conditions were optimised to enable the efficient automated synthesis of several carboxyfluorescein-label led 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-diniannosylated peptides) for biological evaluation.

• 出版日期2009-7-1