Synthesis and conformational analysis of poly(phenylacetylene)s with serinol-tethered carbohydrate appendages
We synthesized phenylacetylenes containing β-lactoside, β-cellobioside, or β-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains by serinol spacers. Because similar glycosyl...
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Published in: | Carbohydrate research Vol. 481; pp. 23 - 30 |
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Main Authors: | , , , , , , , , , |
Format: | Journal Article |
Language: | English |
Published: |
Netherlands
Elsevier Ltd
15-07-2019
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Subjects: | |
Online Access: | Get full text |
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Summary: | We synthesized phenylacetylenes containing β-lactoside, β-cellobioside, or β-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains by serinol spacers. Because similar glycosyl serinol units are found in the natural glycosphingolipids in cell membranes, the densely packed carbohydrate clusters along the poly (phenylacetylene) mainchains act as molecular mimics of cell surface glycoclusters. We analyzed the conformation of the glycosylated poly (phenylacetylene)s using circular dichroism spectroscopy, and found that the spatial carbohydrate packing within the glycoclusters changed on the addition of salts.
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•Poly (phenylacetylene)s containing multiple carbohydrates with serinol spacers•Helical structures revealed by circular dichroic spectroscopy analysis•Salt-induced conformational change of the glycosylated poly (phenylacetylene)s |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/j.carres.2019.06.002 |