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 …

The impact of oxacarbenium ion conformers on the stereochemical outcome of glycosylations

MTC Walvoort, J Dinkelaar, LJ van den Bos… - Carbohydrate …, 2010 - Elsevier
The search for stereoselective glycosylation reactions has occupied synthetic carbohydrate
chemists for decades. Traditionally, most attention has been focused on controlling the SN2 …

Mechanism of chemical O-glycosylation: from early studies to recent discoveries

LK Mydock, AV Demchenko - Organic & biomolecular chemistry, 2010 - pubs.rsc.org
Mechanism of chemical O-glycosylation : from early studies to recent discoveries - Organic &
Biomolecular Chemistry (RSC Publishing) DOI:10.1039/B916088D Royal Society of Chemistry …

The influence of acceptor nucleophilicity on the glycosylation reaction mechanism

S Van der Vorm, T Hansen, HS Overkleeft… - Chemical …, 2017 - pubs.rsc.org
A set of model nucleophiles of gradually changing nucleophilicity is used to probe the
glycosylation reaction mechanism. Glycosylations of ethanol-based acceptors, bearing …

A Visible‐Light‐Promoted O‐Glycosylation with a Thioglycoside Donor

ML Spell, K Deveaux, CG Bresnahan… - Angewandte Chemie …, 2016 - Wiley Online Library
Visible‐light irradiation of 4‐p‐methoxyphenyl‐3‐butenylthioglucoside donors in the
presence of Umemoto's reagent and alcohol acceptors serves as a mild approach to O …

Chemoenzymatic modular assembly of O-GalNAc glycans for functional glycomics

S Wang, C Chen, MR Gadi, V Saikam, D Liu… - Nature …, 2021 - nature.com
O-GalNAc glycans (or mucin O-glycans) play pivotal roles in diverse biological and
pathological processes, including tumor growth and progression. Structurally defined O …

Total Synthesis of Trisaccharide Repeating Unit of Staphylococcus aureus Type 8 (CP8) Capsular Polysaccharide

D Rai, SS Kulkarni - Organic Letters, 2023 - ACS Publications
Herein, we report a highly efficient total synthesis of Staphylococcus aureus type 8
trisaccharide repeating unit in a lesser number of steps and high stereoselectivity. The …

Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry

D Crich - The Journal of organic chemistry, 2011 - ACS Publications
This Perspective outlines work in the Crich group on the diastereoselective synthesis of the
so-called difficult classes of glycosidic bond: the 2-deoxy-β-glycopyranosides, the β …

Automated solution-phase synthesis of β-1, 4-mannuronate and β-1, 4-mannan

SL Tang, NLB Pohl - Organic letters, 2015 - ACS Publications
The first automated solution-phase synthesis of β-1, 4-mannuronate and β-1, 4-mannan
oligomers has been accomplished by using a β-directing C-5 carboxylate strategy. By …

Progress and challenges in the synthesis of sequence controlled polysaccharides

G Fittolani, T Tyrikos-Ergas, D Vargová… - Beilstein Journal of …, 2021 - beilstein-journals.org
The sequence, length and substitution of a polysaccharide influence its physical and
biological properties. Thus, sequence controlled polysaccharides are important targets to …