Exploiting non-covalent interactions in selective carbohydrate synthesis

CCJ Loh - Nature Reviews Chemistry, 2021 - nature.com
Non-covalent interactions (NCIs) are a vital component of biological bond-forming events,
and have found important applications in multiple branches of chemistry. In recent years, the …

Acceptor reactivity in glycosylation reactions

S Van Der Vorm, T Hansen, JMA Van Hengst… - Chemical Society …, 2019 - pubs.rsc.org
The outcome of a glycosylation reaction critically depends on the reactivity of all reaction
partners involved: the donor glycoside (the electrophile), the activator (that generally …

Mapping the relationship between glycosyl acceptor reactivity and glycosylation stereoselectivity

S van der Vorm, JMA van Hengst, M Bakker… - Angewandte …, 2018 - Wiley Online Library
The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for
the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where …

Regioselective acylation, alkylation, silylation and glycosylation of monosaccharides

J Lawandi, S Rocheleau, N Moitessier - Tetrahedron, 2016 - Elsevier
Many organisms use sugars as building blocks for more complex structures in nature such
as cellulose in plants and chitin in crustaceans. To construct these large polysaccharides …

Synthetic, zwitterionic Sp1 oligosaccharides adopt a helical structure crucial for antibody interaction

Q Zhang, A Gimeno, D Santana, Z Wang… - ACS central …, 2019 - ACS Publications
The zwitterionic Streptococcus pneumoniae serotype 1 polysaccharide (Sp1) is an important
anchor point for our immune system to act against streptococcal infections. Antibodies can …

[HTML][HTML] Installation of Electron Donating Protective Groups, a Strategy for Glycosylating Unreactive Thioglycosyl Acceptors using the Pre-activation Based …

Y Zeng, Z Wang, D Whitfield… - The Journal of organic …, 2008 - ncbi.nlm.nih.gov
The pre-activation based chemoselective glycosylation is a powerful strategy for
oligosaccharide synthesis with its successful application in assemblies of many complex …

6-O-Benzyl- and 6-O-Silyl-N-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxyglucosides:  Effective Glycosyl Acceptors in the Glucosamine 4-OH Series. Effect of …

D Crich, AU Vinod - The Journal of Organic Chemistry, 2005 - ACS Publications
The 4-OH groups of both α-and β-methyl glycosides of N-acetylglucosamine, protected with
an oxazolidinone spanning the nitrogen and O-3, and bearing benzyl or silyl protection on O …

Synthetic access toward the diverse ginsenosides

J Yu, J Sun, Y Niu, R Li, J Liao, F Zhang, B Yu - Chemical Science, 2013 - pubs.rsc.org
All the possible types of the protopanaxatriol and protopanaxadiol glycosides, the major
active yet extremely heterogeneous principles of ginsengs, could be accessed by the …

Galacturonic acid lactones in the synthesis of all trisaccharide repeating units of the zwitterionic polysaccharide Sp1

AE Christina, LJ van den Bos… - The Journal of …, 2011 - ACS Publications
A modular approach toward the synthesis of all possible trimer repeating units of the type 1
capsular polysaccharide of Streptococcus pneumonia, Sp1, is described. This zwitterionic …

Uronic acids in oligosaccharide and glycoconjugate synthesis

JDC Codée, AE Christina, MTC Walvoort… - Reactivity Tuning in …, 2011 - Springer
This chapter describes the assembly of uronic acid containing oligosaccharides and
glycoconjugates. Two strategies are available to access these target molecules, namely a …