Journal
ACS CATALYSIS
Volume 8, Issue 6, Pages 4986-4990Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b00992
Keywords
aerobic oxidation; deamination; organocatalysis; ortho-naphthoquinone; prototropic rearrangement
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Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIP) [NRF-2015R1A5A1008958, NRF-2015R1C1A2A01053504]
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An ortho-naphthoquinone-catalyzed oxidative deamination reaction has been developed where the molecular oxygen and water serve as the sole oxidant and nucleophile. The current aerobic deamination reaction proceeds via the ketimine formation between ortho-naphthoquinones and amines followed by the prototropic rearrangement and hydrolysis by water, representing a biomimetic oxidative deamination of amine species in the human body by the liver and kidneys. The compatibility of orthonaphthoquinone organocatalysts with molecular oxygen and water opens up a new biomimetic catalyst system that can function as versatile deaminases for a variety of amine-containing molecules such as amino acids and DNA nuclear bases.
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