Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates

Róisín O’Flaherty; Trinidad Velasco-Torrijos

doi:10.1055/s-0036-1591902

Synlett, Table of Contents

Synlett 2018; 29(07): 904-907
DOI: 10.1055/s-0036-1591902

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Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates

Róisín O’Flaherty

^aDepartment of Chemistry, Maynooth University, Maynooth, Co. Kildare, Ireland Email: trinidad.velascotorrijos@mu.ie

^bNIBRT GlycoScience Group, NIBRT - The National Institute for Bioprocessing Research and Training, Fosters Avenue, Mount Merrion, Blackrock, Co. Dublin, Ireland

,

Trinidad Velasco-Torrijos *

^aDepartment of Chemistry, Maynooth University, Maynooth, Co. Kildare, Ireland Email: trinidad.velascotorrijos@mu.ie

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Abstract

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Abstract

A series of glycosylated α-azido amino acids was synthesized as precursors for neoglycoconjugates, a class of important biomolecules for drug discovery, and sensor development. The synthetically challenging 1,2-cis α-galactosylated species described herein were designed as building blocks in the synthesis of analogues of α-galactosyl ceramide, a potent immunomodulator. A benzyl-protected 1,2,3-triazolyl α-galactosyl-l-serine derivative was prepared using copper azide alkyne cycloaddition to showcase the potential of glycosylated α-azido amino acids in neoglycoconjugate design.

Key words

α-azido amino acid - glycosylation - neoglycoconjugates 1,2,3-triazolyl glycosides - CuAAC reaction

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References

References and Notes
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