Journal ArticleDOI
Phenylalanine Aminomutase-Catalyzed Addition of Ammonia to Substituted Cinnamic Acids: a Route to Enantiopure alpha- and beta-Amino Acids
Wiktor Szymanski,Bian Wu,Barbara Weiner,Stefaan Marie André De Wildeman,Ben L. Feringa,Dick B. Janssen +5 more
TLDR
A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates, which has a broad scope and yields substituted alpha- and beta-phenylalanines with excellent enantiomeric excess.Abstract:
An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.read more
Citations
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Journal ArticleDOI
Recent advances in the catalytic asymmetric synthesis of β-amino acids
TL;DR: The progress in catalytic asymmetric synthesis of beta-amino acids is discussed, covering the literature since 2002 and the most important synthetic methods, such as hydrogenation, the Mannich reaction and conjugate additions are covered.
Journal ArticleDOI
Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
Jamie M. Neely,Tomislav Rovis +1 more
TL;DR: Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism, giving 5-substituted pyridines with very high levels of regioselectivity.
Journal ArticleDOI
Enzymatic asymmetric synthesis of chiral amino acids.
TL;DR: This review provides an overview of the reported methods for enzymatic asymmetric synthesis of chiral amino acids, including asymmetric reductive amination of keto acids, asymmetric transfer of an amino group to keto fatty acids, enantioselective addition of ammonia to α,β-unsaturated acids, and aldol condensation ofan amino acid to aldehydes.
Journal ArticleDOI
Recent progress in industrial biocatalysis.
TL;DR: This review focuses on selected examples integrating biocatalysts into a variety of industrially interesting processes ranging from the manufacture of smaller, chiral speciality chemicals to the synthesis of more complex pharmaceutical intermediates.
Journal ArticleDOI
Ammonia lyases and aminomutases as biocatalysts for the synthesis of α-amino and β-amino acids
TL;DR: The aim of this review is to review recent progress in the application of ammonia lyase and aminomutase enzymes to prepare enantiomerically pure α-amino and β-aminos acids.
References
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A survey of Hammett substituent constants and resonance and field parameters
Corwin Hansch,A. Leo,R. W. Taft +2 more
TL;DR: The Hammett equation has been widely used for the study and interpretation of organic reactions and their mechanisms as mentioned in this paper, and it is astonishing that u constants, obtained simply from the ionization of organic acids in solution, can frequently predict successfully equilibrium and rate constants for a variety of families of reactions in solution.
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β-Peptidic Peptidomimetics
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TL;DR: This Account presents examples of beta-peptidic compounds binding, as agonists or antagonists (inhibitors), to (i) major histocompatibility complex (MHC) proteins (immune response), (ii) the lipid-transport protein SR-B1 (cholesterol uptake from the small intestine), (iii) the core of interleukin-8 ( inflammation), and (iv) the oncoprotein RDM2.