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Title: Cyclooligomerisation of azido-alkyne-functionalised sugars: synthesis of 1,6-linked cyclic pseudo-galactooligosaccharides and assessment of their sialylation by Trypanosoma cruzi trans-sialidase
Authors: Campo, Vanessa L.
Carvalho, Ivone
Da Silva, Carlos H. T. P.
Schenkman, Sergio [UNIFESP]
Hill, Lionel
Nepogodiev, Sergey A.
Field, Robert A.
John Innes Ctr
Universidade de São Paulo (USP)
Universidade Federal de São Paulo (UNIFESP)
Issue Date: 1-Oct-2010
Publisher: Royal Soc Chemistry
Citation: Chemical Science. Cambridge: Royal Soc Chemistry, v. 1, n. 4, p. 507-514, 2010.
Abstract: 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.
ISSN: 2041-6520
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Appears in Collections:Em verificação - Geral

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