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Issue 10, 2011
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Synthesis of glycosylated peptides by NCA polymerization for recognition of human T-cells

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Abstract

Peracetylated sugars (glucose, mannose, galactose) were attached via a thiourea linker to the ε-amino group of α-BOC-lysine and α-Z-lysine. After transformation to the N-carboxyanhydride (NCA), the product was copolymerized with both PEGylated lysine-NCA and ε-TFA-lysine-NCA by both tertiary amine and nickel complex catalysts. The resulting statistical copolypeptides are water-soluble after global deprotection and show an α-helical secondary structure. Fluorescein isothiocyanate (FITC) was then coupled to the free ε-NH2 groups of the lysine repeating units. The galactosylated fluorescent peptides are specifically incorporated in human T lymphocytes at 37 °C, as shown by flow cytometry and fluorescence microscopy. Therefore they are potentially useful for selective staining of cells or targeted drug delivery.

Graphical abstract: Synthesis of glycosylated peptides by NCA polymerization for recognition of human T-cells

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Publication details

The article was received on 29 Apr 2011, accepted on 03 Jul 2011 and first published on 28 Jul 2011


Article type: Paper
DOI: 10.1039/C1PY00187F
Citation: Polym. Chem., 2011,2, 2239-2248
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    Synthesis of glycosylated peptides by NCA polymerization for recognition of human T-cells

    T. Stöhr, A. Blaudszun, U. Steinfeld and G. Wenz, Polym. Chem., 2011, 2, 2239
    DOI: 10.1039/C1PY00187F

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