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1. (Article ID: 3376)
Liu C, Skogman F, Cai Y, Lowary TL
Synthesis of the 'primer-adaptor' trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide
Carbohydrate Research 342(18) (2007)
2818-2825
Described is the synthesis of the trisaccharide α-D-Manp-(1→3)-α-D-Manp-(1→3)-β-D-GlcpNAcO(CH(2))(8)N(3), the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1→3)-α-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates.
Lipopolysaccharide, synthesis, oligosaccharide, Escherichia coli, Klebsiella pneumoniae, neoglycoconjugate
NCBI PubMed ID: 17892864Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tlowary
ualberta.ca
Institutions: Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, AB, Canada AB T6G 2G2
Methods: 13C NMR, 1H NMR, NMR-2D, chemical methods
The publication contains the following compound(s):
- Compound ID: 7519
Structure type: oligomer
Aglycon: (CH2)8N3
Reference(s) to other database(s): GTC:G97599KE, GlycomeDB:
34955
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