NDLI: Synthesis and preliminary biological evaluation of carba analogues from Neisseria meningitidis A capsular polysaccharide.

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Synthesis and preliminary biological evaluation of carba analogues from Neisseria meningitidis A capsular polysaccharide.

Content Provider	Semantic Scholar
Author	Gao, Qi Ming Zaccaria, Cristina Tontini, Marta Poletti, Laura Costantino, Paolo Lay, Luigi
Copyright Year	2012
Abstract	The Gram-negative encapsulated bacterium Neisseria meningitidis type A (MenA) is a major cause of meningitis in developing countries, especially in the sub-Saharan region of Africa. The development and manufacture of an efficient glycoconjugate vaccine against MenA is greatly hampered by the poor hydrolytic stability of its capsular polysaccharide, consisting of (1→6)-linked 2-acetamido-2-deoxy-α-d-mannopyranosyl phosphate repeating units. The replacement of the ring oxygen with a methylene group to get a carbocyclic analogue leads to the loss of the acetalic character of the phosphodiester and consequently to the enhancement of its chemical stability. Here we report the synthesis of oligomers (mono-, di- and trisaccharide) of carba-N-acetylmannosamine-1-O-phosphate as candidates for stabilized analogues of the corresponding fragments of MenA capsular polysaccharide. Each of the synthesized compounds contains a phosphodiester-linked aminopropyl spacer at its reducing end to allow for protein conjugation. The inhibition abilities of the synthetic molecules were investigated by a competitive ELISA assay, showing that only the carba-disaccharide is recognized by a polyclonal anti-MenA serum with an affinity similar to a native MenA oligosaccharide with average polymerization degree of 3.
File Format	PDF HTM / HTML
DOI	10.1039/c2ob25222h
PubMed reference number	22850927
Journal	Medline
Volume Number	10
Issue Number	33
Alternate Webpage(s)	http://repository.unair.ac.id/25640/17/17.%20Daftar%20Pustaka.pdf
Alternate Webpage(s)	http://www.rsc.org/suppdata/ob/c2/c2ob25222h/c2ob25222h.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c2ob25222h
Journal	Organic & biomolecular chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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