Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

• Malamatenia D. Manouilidou,
• Yannis G. Lazarou,
• Irene M. Mavridis and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 774–783, doi:10.3762/bjoc.10.73

• , 15310 Greece. Tel. +30210 6503796, Fax: +30 210 6511766 10.3762/bjoc.10.73 Abstract β-Cyclodextrin (β-CD) dimers have been prepared using the bioorthogonal Staudinger ligation for the first time. In addition to a known linker, methyl 2-(diphenylphosphanyl)terephthalate, a doubly active linker was

• ]. The intermediate, a phosphaza ylide (1, Scheme 1a) is readily formed with loss of nitrogen gas, while subsequent hydrolysis yields the corresponding amine and phosphine oxide. A variant of this reaction is the Staudinger ligation [4], a bioorthogonal reaction that has become an important tool of

Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• at the termini of mammalian cell-surface glycostructures, which participate in essential interaction processes including adhesion of pathogens prior to infection and immunogenicity. Here we present the synthesis and bioorthogonal metabolic incorporation of the sialic acid analogue N-(1-oxohex-5-ynyl

• )neuraminic acid (Neu5Hex) into the cell-surface glycocalyx of a human larynx carcinoma cell line (HEp-2) and its fluorescence labelling by click chemistry. Keywords: bioorthogonal metabolic glycoengineering; click chemistry; sialic acid; Introduction The surface of eukaryotic cells is heavily covered with

• processes involved in infection, inflammation or tumor formation [1]. Recent studies have shown that the surface of a T-cell line (Jurkat), Chinese hamster ovary (CHO) cells, cervical adenocarcinoma (HeLa) cells as well as many other cell types can be labelled with bioorthogonal, that is metabolically inert