Primary structure of glycans by NMR spectroscopy

C Fontana, G Widmalm - Chemical Reviews, 2023 - ACS Publications
Glycans, carbohydrate molecules in the realm of biology, are present as biomedically
important glycoconjugates and a characteristic aspect is that their structures in many …

Mechanisms of stereodirecting participation and ester migration from near and far in glycosylation and related reactions

AA Hettikankanamalage, R Lassfolk, FS Ekholm… - Chemical …, 2020 - ACS Publications
This review is the counterpart of a 2018 Chemical Reviews article (Adero, PO; Amarasekara,
H.; Wen, P.; Bohé, L.; Crich, D. Chem. Rev. 2018, 118, 8242–8284) that examined the …

The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface

PO Adero, H Amarasekara, P Wen, L Bohé… - Chemical …, 2018 - ACS Publications
A critical review of the state-of-the-art evidence in support of the mechanisms of
glycosylation reactions is provided. Factors affecting the stability of putative oxocarbenium …

Influence of side chain conformation on the activity of glycosidase inhibitors

PS Tseng, C Ande, KW Moremen… - Angewandte Chemie, 2023 - Wiley Online Library
Substrate side chain conformation impacts reactivity during glycosylation and glycoside
hydrolysis and is restricted by many glycosidases and glycosyltransferases during catalysis …

En route to the transformation of glycoscience: A chemist's perspective on internal and external crossroads in glycochemistry

D Crich - Journal of the American Chemical Society, 2020 - ACS Publications
Carbohydrate chemistry is an essential component of the glycosciences and is fundamental
to their progress. This Perspective takes the position that carbohydrate chemistry, or …

A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art

L Bohé, D Crich - Carbohydrate research, 2015 - Elsevier
An overview of recent advances in glycosylation with particular emphasis on mechanism is
presented. The mounting evidence for both the existence of glycosyl oxocarbenium ions as …

A 3,4‐trans‐Fused Cyclic Protecting Group Facilitates α‐Selective Catalytic Synthesis of 2‐Deoxyglycosides

EI Balmond, D Benito‐Alifonso, DM Coe… - Angewandte …, 2014 - Wiley Online Library
A practical approach has been developed to convert glucals and rhamnals into
disaccharides or glycoconjugates with high α‐selectivity and yields (77–97%) using a trans …

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 …

Conformationally constrained glycosyl donors as tools to control glycosylation outcomes

RA Jeanneret, SE Johnson… - The Journal of Organic …, 2020 - ACS Publications
The stereoselective synthesis of oligosaccharides remains one of the biggest challenges in
carbohydrate chemistry. Many factors, including reaction conditions and the type of glycosyl …

Synthesis and stereocontrolled equatorially selective glycosylation reactions of a pseudaminic acid donor: Importance of the side-chain conformation and …

B Dhakal, D Crich - Journal of the American Chemical Society, 2018 - ACS Publications
Pseudaminic acid is an amino deoxy sialic acid whose glycosides are essential components
of many pathogenic Gram-negative bacterial cell walls including those from Pseudomonas …