NDLI: Synthesis of stable C-phosphonate analogues of Neisseria meningitidis group A capsular polysaccharide structures using modified Mitsunobu reaction conditions

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Synthesis of stable C-phosphonate analogues of Neisseria meningitidis group A capsular polysaccharide structures using modified Mitsunobu reaction conditions

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Organic & Biomolecular Chemistry Vol - 4 Issue - 19

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Synthesis of stable C-phosphonate analogues of Neisseria meningitidis group A capsular polysaccharide structures using modified Mitsunobu reaction conditions

Content Provider	Royal Society of Chemistry (RSC)
Author	Oscarson, Stefan Slättegård, Rikard Teodorović, Peter
Copyright Year	2006
Abstract	Examples of synthetic C-phosphonate analogues of microbial polysaccharide structures containing inter-residue phosphodiester linkages are most rare. The successful construction of such analogues of the Neisseria meningitidis Group A capsular polysaccharide is described. Using a modified Mitsunobu reaction (tris(4-chlorophenyl)phosphine, DIAD, excess of Et3N) between an anomeric C-phosphonate monoester and a 6-OH ManNAc acceptor a high yield (88%) of a dimer was obtained. Transformation of the dimer into a new 6-OH acceptor through deacetylation and further reaction with the elongating C-phosphonate monomer employing the same conditions afforded the trimer in 92% yield. Iteration of the procedure then afforded the tetramer with a coupling yield of 85%. The di-, tri- and tetramer were deprotected to give target structures ready for conjugation to a carrier protein and subsequent immunological evaluation.
Starting Page	4485
Ending Page	4490
Page Count	6
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	4
Issue Number	24
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b614038f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Protein trimer Phosphine Mitsunobu reaction Phosphodiester bond Mitsunobu Protein dimer Protein Ester Tetramer Neisseria Monomer Polysaccharide Diisopropyl azodicarboxylate
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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