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

被引:32
作者
Stoehr, Thomas [1 ]
Blaudszun, Andre-Rene [2 ]
Steinfeld, Ute [2 ]
Wenz, Gerhard [1 ]
机构
[1] Univ Saarland, D-66123 Saarbrucken, Germany
[2] Univ Saarland, KIST Europe, D-66123 Saarbrucken, Germany
关键词
BETA-CYCLODEXTRIN; L-LYSINE; BINDING; CHEMISTRY; PROTEIN; GUEST; POLYPEPTIDES; ACTIVATION; EXPRESSION; DESIGN;
D O I
10.1039/c1py00187f
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Peracetylated sugars (glucose, mannose, galactose) were attached via a thiourea linker to the 3-amino group of alpha-BOC-lysine and alpha-Z-lysine. After transformation to the N-carboxyanhydride (NCA), the product was copolymerized with both PEGylated lysine-NCA and epsilon-TFA-lysine-NCA by both tertiary amine and nickel complex catalysts. The resulting statistical copolypeptides are water-soluble after global deprotection and show an alpha-helical secondary structure. Fluorescein isothiocyanate (FITC) was then coupled to the free epsilon-NH2 groups of the lysine repeating units. The galactosylated fluorescent peptides are specifically incorporated in human T lymphocytes at 37 degrees C, as shown by flow cytometry and fluorescence microscopy. Therefore they are potentially useful for selective staining of cells or targeted drug delivery.
引用
收藏
页码:2239 / 2248
页数:10
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