1217264-32-8Relevant articles and documents
Chemoselective reagents for covalent capture and display of glycans in microarrays
Clo, Emiliano,Blixt, Ola,Jensen, Knud J.
scheme or table, p. 540 - 554 (2010/06/11)
Glycobiology has made very significant progress in the past: decades. However, further progress will significantly depend on the establishment of novel methods for miniaturized, high-throughput analysis of glycan-protein interactions. Robust: solid-phase chemical tools and new, chemoselective reagents for biologically meaningful display of surface-immobilized glycans are likely to play a key role. Here we present four new bifunctional linkers that allow highly chemoselective capture of unprotected glycans in solution to form glycan-linker conjugates for direct construction of glycan microarrays (glycochips). The bifunctional linkere carry O-liriked aminooxy moieties, some with N-substituents at one end and an amino group at the other. In addition, they contain a substituted benzene ring for UV traceability and improved pari-fication of glycan-linker conjugates. NMR spectroscopic studies in solution proved that N-substituted amlnooxy linkers provided model glycan-linker conjugates with the β-glucopyranoside configuration, i. e. the ring-closed form required for biological, recognition. Then an ensemble of glycan-linker conjugates were assembled from mannobiose, lactose, and N-acetyl-lactosamine and used for covalent printing of glycan microarrays. The stability of oximes were studied both in solution and on-chip. In solution, two of the linkers provided glycan-linker conjugates with a remarkable stability at pH 4 or higher, on-chip this relative stability was upheld. Two of the linkers, with different properties, are recommended for the glycobiology toolbox for the construction of glycan microarrays from unprotected glycans.
