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Issue 10, 2012
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Chemoselective hydroxyl group transformation: an elusive target

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The selective reaction of one functional group in the presence of others is not a trivial task. A noteworthy amount of research has been dedicated to the chemoselective reaction of the hydroxyl moiety. This group is prevalent in many biologically important molecules including natural products and proteins. However, targeting the hydroxyl group is difficult for many reasons including its relatively low nucleophilicity in comparison to other ubiquitous functional groups such as amines and thiols. Additionally, many of the developed chemoselective reactions cannot be used in the presence of water. Despite these complications, chemoselective transformation of the hydroxyl moiety has been utilized in the synthesis of complex natural product derivatives, the reaction of tyrosine residues in proteins, the isolation of natural products and is the mechanism of action of myriad drugs. Here, methods for selective targeting of this group, as well as applications of several devised methods, are described.

Graphical abstract: Chemoselective hydroxyl group transformation: an elusive target

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Publication details

The article was received on 29 Mar 2012, accepted on 18 May 2012 and first published on 22 May 2012

Article type: Review Article
DOI: 10.1039/C2MB25122A
Citation: Mol. BioSyst., 2012,8, 2484-2493
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    Chemoselective hydroxyl group transformation: an elusive target

    D. J. Trader and E. E. Carlson, Mol. BioSyst., 2012, 8, 2484
    DOI: 10.1039/C2MB25122A

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