8 高分子担体を用いた糖鎖合成における新手法の開発(口頭発表の部)

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Solid phase synthesis is now widely recognised as the edge technology for rapid and efficient oligosaccharide construction. However, it has several disadvantages which should be overcome, i) the reduced reactivity of substrates, ii) the difficulty of real-time reaction monitoring, iii) limitations on ability of scale-up reactions, iv) purification of the desired compounds. We choose the PEG (Ave M. W. 550) as a polymer support. It gives homogeneous conditions in reaction mixture, so the reactivity of substrate bound to PEG does not diminished. The scale up of the reaction is possible because the low molecular weight of PEG. Due to its high polarity of PEG, purification of PEG bound sugar was quite simple using silica gel column chromatography. Using the nitro group introduced linker, which is quite stable under typical glycosylation reactions, the oligosaccharide was synthesised on PEG. The monitoring of the glycosylation reaction was performed by MALDI-TOF MAS based on the characteristic signal pattern which derives from normal distribution of PEG chain length. The reaction monitoring of deprotection of chloroacetyl group was performed by colorimetric assay by use of (p-nitrobenzyl)pyridine. Chloroacetyl group was selectively reacts with (p-nitrobenzyl) pyridine to give red color under basic conditions. The reaction was semi-quantified by use of NIH Image software. "Catch and release strategy" for the purification of polymer supported oligosaccharide was developed. Solid phase bound cysteine captures the glycosylated product having the chloroacetyl group. Cleavage reaction of Fmoc group releases the sugar via intramolcular cyclization process into the solution phase. By repetition of glycosyltion/capture/release cycle, the poly(lactosamine) was synthesized on polymer support.
天然有機化合物討論会の論文
2001-09-01

8 高分子担体を用いた糖鎖合成における新手法の開発(口頭発表の部)

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