New syntheses of thiosaccharides utilizing substitution reactions

R Bielski, D Mencer - Carbohydrate Research, 2023 - Elsevier
Novel synthetic methods published since 2005 affording carbohydrates containing sulfur
atom (s) are reviewed. The review is divided to subchapters based on the position of sulfur …

Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions

T Hansen, H Elferink, JMA van Hengst… - Nature …, 2020 - nature.com
Controlling the chemical glycosylation reaction remains the major challenge in the synthesis
of oligosaccharides. Though 1, 2-trans glycosidic linkages can be installed using …

Defining the SN1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations

T Hansen, L Lebedel, WA Remmerswaal… - ACS central …, 2019 - ACS Publications
The broad application of well-defined synthetic oligosaccharides in glycobiology and
glycobiotechnology is largely hampered by the lack of sufficient amounts of synthetic …

Catalyst-controlled regiodivergent synthesis of 1-and 3-thiosugars with high stereoselectivity and chemoselectivity

Y Liu, Y Jiao, H Luo, N Huang, M Lai, K Zou… - ACS Catalysis, 2021 - ACS Publications
An effective regiodivergent synthesis toward 1-and 3-thiosugars was achieved through
palladium and cobalt catalysis, respectively. β-1-Thiosugars were obtained from 3, 4-O …

Halogen atom participation in guiding the stereochemical outcomes of acetal substitution reactions

KM Demkiw, WA Remmerswaal… - Angewandte Chemie …, 2022 - Wiley Online Library
Acetal substitution reactions of α‐halogenated five‐and six‐membered rings can be highly
stereoselective. Erosion of stereoselectivity occurs as nucleophilicity increases, which is …

A mass‐spectrometry‐based modelling workflow for accurate prediction of IgG antibody conformations in the gas phase

K Hansen, AM Lau, K Giles, JM McDonnell… - Angewandte …, 2018 - Wiley Online Library
Immunoglobulins are biomolecules involved in defence against foreign substances.
Flexibility is key to their functional properties in relation to antigen binding and receptor …

Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues

M Guinan, N Huang, CS Hawes, MA Lima… - Organic & …, 2022 - pubs.rsc.org
Analogues of the canonical nucleosides required for nucleic acid synthesis have a
longstanding presence and proven capability within antiviral and anticancer research. 4 …

Competing C‐4 and C‐5‐acyl stabilization of uronic acid glycosyl cations

H Elferink, WA Remmerswaal… - … A European Journal, 2022 - Wiley Online Library
Uronic acids are carbohydrates carrying a terminal carboxylic acid and have a unique
reactivity in stereoselective glycosylation reactions. Herein, the competing intramolecular …

Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses …

S van der Vorm, T Hansen… - … A European Journal, 2019 - Wiley Online Library
The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the
stereochemical course of SN1 reactions taking place on these reactive intermediates is …

4-thioribose analogues of adenosine diphosphate ribose (ADPr) peptides

JM Madern, J Voorneveld, JGM Rack… - Organic …, 2023 - ACS Publications
Adenosine diphosphate (ADP) ribosylation is an important post-translational modification
(PTM) that plays a role in a wide variety of cellular processes. To study the enzymes …