Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: melioidosis [ICD11:
1C42 
, ICD11:
XN3LD ];
glanders [ICD11:
1B92 , ICD11:
XN6Y3 ];
infection due to Burkholderia pseudomallei [ICD11:
XN3LD ];
infection due to Burkholderia mallei [ICD11:
XN6Y3 ]
The structure was elucidated in this paperNCBI PubMed ID: 24786555Publication DOI: 10.1021/jo500640nJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: charles.gauthier
univ-poitiers.fr
Institutions: Université de Poitiers, Institut de Chimie IC2MP, UMR-CNRS 7285, Équipe Synthèse Organique, 4 rue Michel Brunet, 86073 Poitiers, France
Burkholderia pseudomallei and Burkholderia mallei are potential bioterrorism agents. They express the same capsular polysaccharide (CPS), a homopolymer featuring an unusual [→3)-2-O-acetyl-6-deoxy-β-D-manno-heptopyranosyl-(1→] as the repeating unit. This CPS is known to be one of the main targets of the adaptive immune response in humans and therefore represents a crucial subunit candidate for vaccine development. Herein, the stereoselective synthesis of mono- and disaccharidic fragments of the B. pseudomallei and B. mallei CPS repeating unit is reported. The synthesis of 6-deoxy-β-D-manno-heptosides was investigated using both inter- and intramolecular glycosylation strategies from thio-manno-heptose that was modified with 2-naphthylmethyl (NAP) at C2. We show here that NAP-mediated intramolecular aglycon delivery (IAD) represents a suitable approach for the stereocontrolled synthesis of 6-deoxy-β-D-manno-heptosides without the need for rigid 4,6-O-cyclic protection of the sugar skeleton. The IAD strategy is highly modular, as it can be applied to structurally diverse acceptors with complete control of stereoselectivity. Problematic hydrogenation of the acetylated disaccharides was overcome by using a microfluidic continuous flow reactor.
synthesis, capsular polysaccharide, Burkholderia pseudomallei, Burkholderia mallei
Structure type: oligomer ; 540.2649 [M+H]+
C
23H
42NO
13Location inside paper: p.4616, fig.2, p.4623, scheme 9, compound 3a
Aglycon: 5-amino-1-pentyl
Compound class: CPS
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, glycosylation, ESI-TOF-MS
Synthetic data: chemical
Comments, role: synthetic disaccharide 3 existed as a mixture of C2/C3 (3a/3b) regioisomers [ratio 3a:3b - 1.8:1.0 (MeOD); - 1.0:1.0 (D2O)]
Related record ID(s): 30142, 30519
NCBI Taxonomy refs (TaxIDs): 28450,
13373Reference(s) to other database(s): GTC:G70521VU
Show glycosyltransferases
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
Found 
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