Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 10, Pages 4615-4634Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500640n
Keywords
-
Categories
Funding
- Agence Nationale de la Recherche Programme Jeunes Chercheuses Jeunes Chercheurs [ANR-JCJC-12-JS07-0003-01]
Ask authors/readers for more resources
Burkholderia pseudo mallei 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-beta-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. pseudo mallei and B. mallei CPS repeating unit is reported. The synthesis of 6-deoxy-beta-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-beta-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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available