Aromatic nitration reactions are a cornerstone of organic chemistry, but are challenging to scale due to corrosive reagents and elevated temperatures. The cytochrome P450 TxtE nitrates the indole 4-position of l-tryptophan at room temperature using NO, O and NADPH, and has potential to be developed into a useful aromatic nitration biocatalyst. However, its narrow substrate scope (requiring both the α-amino acid and indole functionalities) have hindered this. Screening of an R59 mutant library of a TxtE-reductase fusion protein identified a variant (R59C) that nitrates tryptamine, which is not accepted by native TxtE. This variant exhibits a broader substrate scope than the wild type enzyme and is able to nitrate a range of tryptamine analogues, with significant alterations to the aromatic and aminoethyl moieties.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8359946 | PMC |
| http://dx.doi.org/10.1002/cbic.202100145 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds.
Molecules
January 2025
Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, China.
A Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling of C-H/N-H, C-H/C-H and N-H/N-H bonds, with the merits of broad substrate scope and high functional group compatibility. Gram-scale experiments demonstrated the potential applications of this reaction.
View Article and Find Full Text PDFMiniaturization Potential of Additive-Manufactured 3D Mechatronic Integrated Device Components Produced by Stereolithography.
Micromachines (Basel)
December 2024
Institute for Factory Automation and Production Systems, Friedrich-Alexander-Universität Erlangen Nürnberg, Egerlandstr. 7-9, 91058 Erlangen, Germany.
Three-dimensional Mechatronic Integrated Devices (3D-MIDs) combine mechanical and electrical functions, enabling significant component miniaturization and enhanced functionality. However, their application in high-temperature environments remains limited due to material challenges. Existing research highlights the thermal stability of ceramic substrates; yet, their reliability under high-stress and complex mechanical loading conditions remains a challenge.
View Article and Find Full Text PDFBroad substrate scope C-C oxidation in cyclodipeptides catalysed by a flavin-dependent filament.
Nat Commun
January 2025
University of St Andrews, School of Biology, North Haugh, Biomolecular Sciences Building, St Andrews, UK.
Cyclic dipeptides are produced by organisms across all domains of life, with many exhibiting anticancer and antimicrobial properties. Oxidations are often key to their biological activities, particularly C-C bond oxidation catalysed by tailoring enzymes including cyclodipeptide oxidases. These flavin-dependent enzymes are underexplored due to their intricate three-dimensional arrangement involving multiple copies of two distinct small subunits, and mechanistic details underlying substrate selection and catalysis are lacking.
View Article and Find Full Text PDF[Transaminases: high-throughput screening a ketone-fluorescent probe and applications].
Sheng Wu Gong Cheng Xue Bao
January 2025
College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, Zhejiang, China.
Transaminases are a class of enzymes that catalyze the transfer of amino between amino acids and keto acids, playing an important role in the biosynthesis of organic amines and the corresponding derivatives. However, natural enzymes often have low catalytic efficiency against non-natural substrates, which limits their widespread applications. Enzyme engineering serves as an effective approach to improve the catalytic properties and thereby expand the application scope of transaminases.
View Article and Find Full Text PDFRegioselective 1,4-Addition of P(O)-H Species to In SituFormed 1-Benzopyrylium Ion from C3-Substituted 2-Chromene Hemiketals to Construct C3-Functionalized C4-Phosphorylated 4-Chromenes.
J Org Chem
January 2025
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, 2025 Chengluo Avenue, Chengdu 610016, P.R. China.
Herein, we report the first example that P(O)-H species including -phosphonates and -phosphine oxides could participate in a highly regioselective 1,4-addition to in situ generated 1-benzopyrylium ion from C3-substituted 2-chromene hemiketals, which provides a brand-new and effective approach for the synthesis of C4-phosphorylated 4-chromenes with diverse C3-functionality (ketone, ester, sulfonyl, aryl, and alkyl groups). In total, the reaction features the use of inexpensive Zn(ClO)·6HO as a catalyst, low catalyst loading (only 5 mol %), mild reaction conditions (60 °C, 10 min to 24 h), and broad substrate scope (46 examples) as well as good to high yields (>90% yield on average). More importantly, mechanistic experiments demonstrated the essential role of the C3-substituent on 2-chromene hemiketals in stabilizing the in situ generated 1-benzopyrylium ion and the regioselective 1,4-addition control.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!