Cytochrome P450-catalyzed insertion of carbenoids into N–H bonds
TLDR
This work demonstrates enzyme-catalyzed insertion of carbenoids into N-H bonds, which has no counterpart in nature, and can be mediated by variants of the cytochrome P450 from Bacillus megaterium.Abstract:
Expanding nature's catalytic repertoire to include reactions important in synthetic chemistry will open new opportunities for ‘green’ chemistry and biosynthesis. We demonstrate the first enzyme-catalyzed insertion of carbenoids into N–H bonds. This type of bond disconnection, which has no counterpart in nature, can be mediated by variants of the cytochrome P450 from Bacillus megaterium. The N–H insertion reaction takes place in water, provides the desired products in 26–83% yield, forms the single addition product exclusively, and does not require slow addition of the diazo component.read more
Citations
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Fabian Schwizer,Yasunori Okamoto,Tillmann Heinisch,Yifan Gu,Michela M. Pellizzoni,Vincent Lebrun,Raphael Reuter,Valentin Köhler,Jared C. Lewis,Thomas R. Ward +9 more
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References
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Journal ArticleDOI
Organic Synthesis with .alpha.-Diazo Carbonyl Compounds
Tao Ye,M. Anthony McKervey +1 more
Book
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
TL;DR: Synthesis of Alpha-Diazocarbonyl Compounds Catalysts for Metal Carbene Transformations Insertion Reactions Intermolecular Cyclopropanation and Related Addition Reactions Intramolecular cyclopropaneation and related addition Reactions Cycloaddition and Substitution Reactions with Aromatic and Heteroaromatic Compounds Generation and Reactions of Ylides from DBCs X-H InsertionReactions of DBC compounds (X = N,O,S,Se,P, Halogen) The
Journal ArticleDOI
The production of fine chemicals by biotransformations.
TL;DR: An analysis of 134 industrial biotransformations reveals that hydrolases and redox biocatalysts are the most prominent categories and the implications of this for future research and development onBiocatalysis are discussed.
Journal ArticleDOI
Recent studies on the reactions of α-diazocarbonyl compounds
Zhenhua Zhang,Jianbo Wang +1 more
TL;DR: New developments of various reactions of α-diazocarbonyl compounds have been reviewed in this article, which primarily focuses on the literatures published since 2003, focusing on the literature published in 2003.
Modern catalytic methods for organic synthesis with diazo compounds
TL;DR: The Wolff Rearrangement and Related Reactions of Alpha-Diazocarbonyl Compounds with Aldehydes and Ketones are discussed in this paper, as well as other Diazocaronyl reactions.