Journal
CHEMICAL SCIENCE
Volume 1, Issue 4, Pages 507-514Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00301h
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Funding
- BBSRC, UK
- FAPESP, Brazil
- CNPq, Brazil
- BBSRC [BBS/E/J/000C0618] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BBS/E/J/000C0618] Funding Source: researchfish
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Cyclic pseudo-galactooligosaccharides were synthesized by cyclooligomerisation of isomeric azido-alkyne derivatives of beta-D-galactopyranose under Cu(I)-catalysed azide-alkyne 1,3-dipolar cycloaddition reaction conditions. The principal products isolated were cyclic dimers and trimers, with lower amounts of cyclic tetramer and pentamer also evident in some cases. Molecular mechanics calculations suggest very compact but flexible structures for the cyclic trimers, with secondary OH groups exposed outside the macrocycle and available for enzymatic glycosylation. The cyclic dimers and trimers represent a new type of acceptor substrate for Trypanosoma cruzi trans-sialidase, giving rise to doubly and triply sialylated glycomacrocycles, respectively.
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