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Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 11, 2797-2800 p.Article in journal (Refereed) Published
Abstract [en]

Incorporation of the fluorogenic l-(7-hydroxycoumarin-4-yl)ethylglycine into proteins is a valuable biological tool. Coumarins are typically accessed via the Pechmann reaction, which requires acidic conditions and lacks substrate flexibility. A Pd-mediated coupling is described between o-methoxyboronic acids and a glutamic acid derived (Z)-vinyl triflate, forming latent coumarins. Global deprotection with BBr3 forms the coumarin scaffold in a single step. This mild and scalable route yielded five analogues, including a probe suitable for use at lower pH.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2017. Vol. 19, no 11, 2797-2800 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-137386DOI: 10.1021/acs.orglett.7b00854ISI: 000402850900006PubMedID: 28497693OAI: oai:DiVA.org:umu-137386DiVA: diva2:1120457
Available from: 2017-07-06 Created: 2017-07-06 Last updated: 2017-07-06Bibliographically approved

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Moodie, Lindon W. K.Kindahl, TomasHedberg, Christian
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