A Divergent Method to Prepare 5‐Amino‐, 5‐ N ‐Acetamido‐, and 5‐ N ‐Glycolylsialosides | Zendy

Boltje Thomas J. | Zendy; Heise Torben | Zendy; Rutjes Floris P. J. T. | Zendy; van Delft Floris L. | Zendy

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A Divergent Method to Prepare 5‐Amino‐, 5‐ N ‐Acetamido‐, and 5‐ N ‐Glycolylsialosides

Author(s) -

Boltje Thomas J.,

Heise Torben,

Rutjes Floris P. J. T.,

van Delft Floris L.

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201300664

Subject(s) - chemistry , sialic acid , substituent , homogeneous , amine gas treating , block (permutation group theory) , stereochemistry , chemical synthesis , combinatorial chemistry , amino acid , biochemistry , organic chemistry , in vitro , physics , geometry , mathematics , thermodynamics

Sialic acids are essential mediators of biological processes involving carbohydrate recognition. A major determinant of sialic acid recognition is the N‐5 substituent, which can be an N ‐acetyl (human), N ‐glycolyl (non‐human), or amine (cancer associated) functionality. Access to homogeneous sialosides with distinct substitution patterns is essential to determine structure–activity relationships. Herein, we report a divergent chemical approach to enable the synthesis of a library of specifically substituted sialosides by using a single sialic acid building block.

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