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.
MeSH terms
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Amides / chemistry
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Amines / chemical synthesis
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Amines / chemistry*
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Amino Acids / chemical synthesis*
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Amino Acids / chemistry
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Arginine / analogs & derivatives*
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Arginine / chemical synthesis
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Catalysis
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Lysine / analogs & derivatives*
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Lysine / chemical synthesis
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Ornithine / analogs & derivatives*
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Ornithine / chemical synthesis
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Oxidation-Reduction
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Ruthenium / chemistry
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Solid-Phase Synthesis Techniques / economics
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Solid-Phase Synthesis Techniques / methods*
Substances
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Amides
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Amines
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Amino Acids
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Ruthenium
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Arginine
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Ornithine
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Lysine