Stereoselective Synthesis of Sialylated Tumor-Associated Glycosylamino Acids | Zendy

Leo Corcilius | Zendy; Richard J. Payne | Zendy

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Stereoselective Synthesis of Sialylated Tumor-Associated Glycosylamino Acids

Author(s) -

Leo Corcilius,

Richard J. Payne

Publication year - 2013

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol402845e

Subject(s) - chemistry , glycopeptide , muc1 , stereoselectivity , glycan , carbohydrate , amino acid , solid phase synthesis , glycoprotein , antigen , stereochemistry , biochemistry , combinatorial chemistry , catalysis , mucin , peptide , immunology , antibiotics , biology

Suitably protected sialyl T(N) and 2,6-sialyl T tumor-associated carbohydrate antigen-derived amino acids have been prepared stereoselectively using an oxazolidinone-derived sialoside donor. These glycosylamino acids can be employed directly in the solid-phase synthesis of glycopeptides, as demonstrated by the efficient preparation of tumor-associated MUC1 glycopeptide fragments.

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