Bousquet E, Khitri M, Lay L, Nicotra F, Panza L, Russo G Capsular polysaccharide of Streptococcus pneumoniae type 19F: synthesis of the repeating unit Carbohydrate Research311(4) (1998)
171-181
NCBI PubMed ID:9825520 Publication DOI:10.1016/s0008-62159800218-3 Journal NLM ID:0043535 Publisher: Elsevier Institutions: Dipartimento di Chimica Organica e Industriale, via Venezian 21, I-20133, Milano, Italy
A new and more versatile synthesis of β-D-ManpNAc-(1→4)-α-D-Glcp-(1→2)-α-L-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages
synthesis, polysaccharide, Streptococcus, Streptococcus pneumoniae, repeating unit, Oligosaccharides, Anomeric sulfoxides, glycosylationcapsular, capsular polysaccharide, glycoconjugate vaccines, sulfoxides, type
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