Synthesis of silica-bound amylose by phosphorolytic elongation of immobilised maltoheptaosyl hydrazides

Maltoheptaoside-alkoxysilane anchor molecules were synthesised by fusing aliphatic ω-Si(OEt 3) hydrazide linkers with maltoheptaose. After immobilisation of the primers on porous silica, support-bound amylose was synthesised by phosphorolytic synthesis. The hydrazone linkage as a pre-formed cleavage...

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Bibliographic Details
Published in:Tetrahedron letters 2002-08, Vol.43 (35), p.6127-6131
Main Author: Breitinger, Hans-Georg
Format: Article
Language:English
Subjects:
hydrazides
immobilised amylose
maltooligosaccharides
phosphorolytic synthesis
silane linkers
silica gel
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Summary:Maltoheptaoside-alkoxysilane anchor molecules were synthesised by fusing aliphatic ω-Si(OEt 3) hydrazide linkers with maltoheptaose. After immobilisation of the primers on porous silica, support-bound amylose was synthesised by phosphorolytic synthesis. The hydrazone linkage as a pre-formed cleavage site allowed removal and subsequent characterisation of immobilised amylose, which showed a broad molecular weight distribution. Under HPLC conditions, amylose assumed a non-helical conformation, making surface interactions and not complexation the primary separation mechanism. ω-Triethoxysilyl-maltoheptaosyl hydrazides were immobilised on porous silica as primers for enzymatic amylose synthesis. Solid-phase-bound amylose could be removed and analysed using the hydrazide bond as a pre-formed cleavage site.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01293-5