Advanced chemical methods for stereoselective sialylation and their applications in sialoglycan syntheses

AM Vibhute, N Komura, HN Tanaka… - The Chemical …, 2021 - Wiley Online Library
Sialic acid is an important component of cell surface glycans, which are responsible for
many vital body functions and should therefore be thoroughly studied to understand their …

[PDF][PDF] Recent strategies for stereoselective sialylation and their application to the synthesis of oligosialosides

S Hanashima - Trends Glycosci. Glycotechnol, 2011 - scholar.archive.org
Sialic acids on the non-reducing terminus of sialylgylcans are abundantly expressed on the
surface of mammalian cells. They play vital roles in cell-cell interactions and during infection …

Synthesis of sialic acid-containing saccharides

AK Adak, CC Yu, CF Liang, CC Lin - Current Opinion in Chemical Biology, 2013 - Elsevier
Highlights•Chemical synthesis provided access to O-linked and S-linked oligosialic
acids.•Oxazolidinone-protected sialyl donors enable α-selective sialylation.•Enzymatic …

Combined effect of the picoloyl protecting group and triflic acid in sialylation

S Escopy, SA Geringer, C De Meo - Organic letters, 2017 - ACS Publications
The stereoselective synthesis of sialosides is still one of the major challenges in
carbohydrate chemistry. The synthesis and glycosidation of novel sialyl donors bearing a …

Recent developments in enzymatic synthesis of modified sialic acid derivatives

CC Yu, SG Withers - Advanced Synthesis & Catalysis, 2015 - Wiley Online Library
Sialic acid‐containing glycans play important roles in biology, but their synthesis by
standard chemical approaches is challenging. Enzymatic assembly is generally a better …

Sialic acid glycoengineering using an unnatural sialic acid for the detection of sialoglycan biosynthesis defects and on-cell synthesis of siglec ligands

C Büll, T Heise, DMH Beurskens… - ACS chemical …, 2015 - ACS Publications
Sialoglycans play a vital role in physiology, and aberrant sialoglycan expression is
associated with a broad spectrum of diseases. Since biosynthesis of sialoglycans is only …

A new C (1)-auxiliary for anomeric stereocontrol in the synthesis of α-sialyl glycosides

JM Haberman, DY Gin - Organic letters, 2001 - ACS Publications
The installation of the novel N, N-dimethylglycolamide ester auxiliary onto the C (1)-position
of protected neuraminic acid donors allows for the exploitation of C (1)-neighboring group …

Enabling chemoenzymatic strategies and enzymes for synthesizing sialyl glycans and sialyl glycoconjugates

X Chen - Accounts of Chemical Research, 2023 - ACS Publications
Conspectus Sialic acids are fascinating negatively charged nine-carbon monosaccharides.
Sialic acid-containing glycans and glycoconjugates are structurally diverse, functionally …

1, 5‐Lactamized Sialyl Acceptors for Various Disialoside Syntheses: Novel Method for the Synthesis of Glycan Portions of Hp‐s6 and HLG‐2 Gangliosides

H Ando, Y Koike, S Koizumi, H Ishida… - Angewandte …, 2005 - Wiley Online Library
The ongoing studies on oligosaccharide synthesis have resulted in the development of
precise synthetic methods by which a large portion of the complex natural oligosaccharides …

Chemoenzymatic synthesis of Neu5Ac9NAc-containing α2–3-and α2–6-linked sialosides and their use for sialidase substrate specificity studies

W Li, A Xiao, Y Li, H Yu, X Chen - Carbohydrate research, 2017 - Elsevier
O-Acetylation of sialic acid (Sia) modulates its recognition by sialic acid-binding proteins and
plays an important role in biological and pathological processes. 9-O-Acetylation is the most …