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Acid-Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.ORCID iD: 0000-0002-9458-4822
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. Univ Massachusetts, Dept Chem, 1 Univ Ave, Lowell, MA 01854 USA;Linnaeus Univ, Dept Chem & Biomed Sci, S-39182 Kalmar, Sweden.ORCID iD: 0000-0002-1533-6514
2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 63, p. 14408-14413Article in journal (Refereed) Published
Abstract [en]

The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized alpha-d-manno- and alpha-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis with allyl alcohol could also be achieved with reasonable selectivity. The presence of small quantities (2.5 vol %) of acetic acid increased the formation of the self-metathesis product while significantly reducing the alkene isomerization process. The catalytic activity was furthermore retained in the presence of large amounts (0.01 mm) of protein, underlining the potential of this carbon-carbon bond-forming reaction under biological conditions. These results demonstrate the potential of directly using unprotected carbohydrate structures in olefin metathesis reactions under mild conditions compatible with biological systems, and thereby enabling their use in, for example, drug discovery and protein derivatization.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019. Vol. 25, no 63, p. 14408-14413
Keywords [en]
carbene ligands, carbohydrates, homogeneous catalysis, olefin metathesis, synthetic methods
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-264872DOI: 10.1002/chem.201903155ISI: 000496034100021PubMedID: 31390489Scopus ID: 2-s2.0-85074340512OAI: oai:DiVA.org:kth-264872DiVA, id: diva2:1379841
Note

QC 20191217

Available from: 2019-12-17 Created: 2019-12-17 Last updated: 2019-12-17Bibliographically approved

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Timmer, BrianRamström, Olof

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