ArticleThe Journal of organic chemistry2019
Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides.
Article in The Journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 25 citations in OpenAlex.
- Structural Principles of Covalent Flavin Modification in Oxidoreductases.Biochemistry · 2026Review
- Article
- 4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides.Organic letters · 2023Article
- Competing C-4 and C-5-Acyl Stabilization of Uronic Acid Glycosyl Cations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides.Angewandte Chemie (International ed. in English) · 2021Article
- Synthesis of Stable NADChembiochem : a European journal of chemical biology · 2020Article
- Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions.Nature communications · 2020Article
- Covalent Modification of the Flavin in Proline Dehydrogenase by Thiazolidine-2-Carboxylate.ACS chemical biology · 2020Article
- Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2-Azidofuranoses, 2-Fluorofuranoses and Methyl Furanosyl Uronates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Defining the SACS central science · 2019Article
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Authors and funding
9 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2- cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio- ribo-furanose appears to be less reactive than its oxo counterpart, the thio- ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio- ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio- ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.