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 …

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 …

Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry

B Dhakal, L Bohé, D Crich - The Journal of organic chemistry, 2017 - ACS Publications
Although the triflate ion is not generally perceived as a nucleophile, many examples of its
behavior as such exist in the literature. This Synopsis presents an overview of such …

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 …

Synthesis and immunological evaluation of disaccharide bearing MUC-1 glycopeptide conjugates with virus-like particles

X Wu, C McKay, C Pett, J Yu, M Schorlemer… - ACS chemical …, 2019 - ACS Publications
Mucin-1 (MUC1) is a highly attractive antigenic target for anticancer vaccines. Naturally
existing MUC1 can contain multiple types of O-linked glycans, including the Thomsen …

Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid

H Liu, Y Zhang, R Wei, G Andolina… - Journal of the American …, 2017 - ACS Publications
Pseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a
component of important cell surface glycans and glycoproteins in various pathogenic …

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 …

Growing impact of sialic acid-containing glycans in future drug discovery

P Bose, MK Jaiswal, SK Singh, RK Singh… - Carbohydrate …, 2023 - Elsevier
In nature, almost all cells are covered with a complex array of glycan chain namely sialic
acids or nuraminic acids, a negatively charged nine carbon sugars which is considered for …

Recent progress on the chemical synthesis of bacterial non-2-ulosonic acids

X Guo, P Li, H Liu, X Li - Organic Chemistry Frontiers, 2023 - pubs.rsc.org
Bacteria resistant to antibiotics present a threat to public health. The bacterial non-2-
ulosonic acids, including pseudaminic acid, legionaminic acid, acinetaminic acid, fusaminic …