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Issue 25, 2015
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Rapid and scalable synthesis of innovative unnatural α,β or γ-amino acids functionalized with tertiary amines on their side-chains

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Abstract

We report a selective ruthenium catalyzed reduction of tertiary amides on the side chain of Fmoc-Gln-OtBu derivatives, leading to innovative unnatural α,β or γ-amino acids functionalized with tertiary amines. Rapid and scalable, this process allowed us to build a library of basic unnatural amino acids at the gram-scale and directly usable for liquid- or solid-phase peptide synthesis. The diversity of available tertiary amines allows us to modulate the physicochemical properties of the resulting amino acids, such as basicity or hydrophobicity.

Graphical abstract: Rapid and scalable synthesis of innovative unnatural α,β or γ-amino acids functionalized with tertiary amines on their side-chains

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Publication details

The article was received on 24 Apr 2015, accepted on 18 May 2015 and first published on 18 May 2015


Article type: Paper
DOI: 10.1039/C5OB00828J
Citation: Org. Biomol. Chem., 2015,13, 7020-7026
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    Rapid and scalable synthesis of innovative unnatural α,β or γ-amino acids functionalized with tertiary amines on their side-chains

    S. Schneider, H. Ftouni, S. Niu, M. Schmitt, F. Simonin and F. Bihel, Org. Biomol. Chem., 2015, 13, 7020
    DOI: 10.1039/C5OB00828J

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