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Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
2017 (engelsk)Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, nr 11, s. 2797-2800Artikkel i tidsskrift (Fagfellevurdert) 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.

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American Chemical Society (ACS), 2017. Vol. 19, nr 11, s. 2797-2800
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URN: urn:nbn:se:umu:diva-137386DOI: 10.1021/acs.orglett.7b00854ISI: 000402850900006PubMedID: 28497693Scopus ID: 2-s2.0-85020035253OAI: oai:DiVA.org:umu-137386DiVA, id: diva2:1120457
Tilgjengelig fra: 2017-07-06 Laget: 2017-07-06 Sist oppdatert: 2023-03-24bibliografisk kontrollert

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

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