Total synthesis of a sialylated and sulfated oligosaccharide from O-linked glycoproteins

The total synthesis of a sialylated and sulfated oligosaccharide 1 representative of a structure occurring in respiratory mucins has been accomplished. Our strategy depends upon the employment of 2-naphthymethyl (NAP) protection for hydroxyl functions. Choice of the well-defined sialyl donor 15 was...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 16; pp. 2773 - 2776
Main Authors Xia, Jie, Piskorz, Conrad F, Alderfer, James L, Locke, Robert D, Matta, Khushi L
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.04.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COMPLEX
MUCIN
LEWIS-X TRISACCHARIDE
GLYCANS
SIALIC-ACID
DERIVATIVES
MOTIF
N-ACETYLNEURAMINIC ACID
STEREOSELECTIVE SYNTHESIS
LE(X)
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Summary:The total synthesis of a sialylated and sulfated oligosaccharide 1 representative of a structure occurring in respiratory mucins has been accomplished. Our strategy depends upon the employment of 2-naphthymethyl (NAP) protection for hydroxyl functions. Choice of the well-defined sialyl donor 15 was made because of its enhanced reactivity over the parent compound 14 for glycosylation.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00261-6