NDLI: Cyclooligomerisation of azido-alkyne-functionalised sugars: synthesis of 1,6-linked cyclic pseudo-galactooligosaccharides and assessment of their sialylation by Trypanosoma cruzi trans-sialidase

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Cyclooligomerisation of azido-alkyne-functionalised sugars: synthesis of 1,6-linked cyclic pseudo-galactooligosaccharides and assessment of their sialylation by Trypanosoma cruzi trans-sialidase

Content Provider	Semantic Scholar
Author	Campo, Vanessa Leiria Carvalho, Ivone Silva, Carlos Henrique Da Schenkman, Sergio Hill, Lionel Nepogodiev, Sergey A. Field, Robert A.
Copyright Year	2010
Abstract	Cyclic pseudo-galactooligosaccharides were synthesized by cyclooligomerisation of isomeric azido-alkyne derivatives of β-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.
Starting Page	507
Ending Page	514
Page Count	8
File Format	PDF HTM / HTML
DOI	10.1039/C0SC00301H
Volume Number	1
Alternate Webpage(s)	https://www.jic.ac.uk/staff/Rob-Field/rafpubstonov2010.pdf
Alternate Webpage(s)	http://www.rsc.org/suppdata/sc/c0/c0sc00301h/c0sc00301h.pdf
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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