Biocatalytic reductive amination as a route to isotopically labelled amino acids suitable for analysis of large proteins by NMR

Rowbotham, Jack S.; Nicholson, Jake H.; Ramirez, Miguel A.; Urata, Kouji; Todd, Peter M. T.; Karunanithy, Gogulan; Lauterbach, Lars; Reeve, Holly A.; Baldwin, Andrew J.; Vincent, Kylie A.

doi:10.1039/d3sc01718d

Cited by 6 publications

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Robust Whole‐Cell‐Based Chemoenzymatic Synthesis of Site‐Selective Deuterated α‐Hydroxy Acids and α‐Amino Acids

Yu,

Liu,

Zhang

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

Deuterated hydroxyl acids and amino acids have been widely utilized in life science, biochemistry and drug development. Site‐selective and stereoselective synthesis of deuterated hydroxyl acids and amino acids remains a significant challenge. Here, we report the development of a robust whole‐cell‐based chemoenzymatic platform for the synthesis of deuterated hydroxyl acids and amino acids from off‐the‐shelf aldehydes in high yields with excellent selectivities and levels of deuteration. The platform delivers products with diverse scaffolds and deuteration patterns, as well as broad scopes with both aromatic and aliphatic side chains. The application of the platform was demonstrated by the concise synthesis of a deuterium‐containing antiparkinson's disease candidate. This platform provides a concrete foundation for accessing amino acid isotopologs for potential applications in research and drug discovery and development.

show abstract

Robust Whole‐Cell‐Based Chemoenzymatic Synthesis of Site‐Selective Deuterated α‐Hydroxy Acids and α‐Amino Acids

Yu,

Liu,

Zhang

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

State‐of‐the‐Art Light‐Driven Hydrogen Generation from Formic Acid and Utilization in Enzymatic Hydrogenations

Peng,

Sakoleva,

Rockstroh

et al. 2024

ChemSusChem

View full text Add to dashboard Cite

A concept of combining photocatalytically generated hydrogen with green enzymatic reductions is demonstrated. The developed photocatalytic formic acid (FA) dehydrogenation setup based on Pt(x)@TiO2 shows unprecedented hydrogen generation activity, which is two orders of magnitude higher than reported values of state‐of‐the‐art systems. Mechanistic studies confirm that hydrogen generation proceeds via a photocatalytic pathway, which is entirely different from purely thermal reaction mechanisms previously reported. The viability of the presented approach is demonstrated by the synthesis of value‐added compounds 3‐phenylpropanal and (2R, 5S)‐dihydrocarvone at ambient pressure and room temperature, which should be applicable for many other hydrogenation processes, e.g., for the preparation of flavours and fragrance compounds, as well as pharmaceuticals.

show abstract

Multifunctionalization of Alkenyl Alcohols via a Sequential Relay Process

Liu,

Wang,

2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Aryl-substituted aliphatic amines are widely recognized as immensely valuable molecules. Consequently, the development of practical strategies for the construction of these molecules becomes increasingly urgent and critical. Here, we have successfully achieved multifunctionalization reactions of alkenyl alcohols in a sequential relay process, which enables transformation patterns of arylamination, deuterated arylamination, and methylenated arylamination to the easy access of multifarious arylalkylamines. Notably, a novel functionalization mode for carbonyl groups has been developed to facilitate the processes of deuterium incorporation and methylene introduction, thereby providing new means for the diverse transformations of carbonyl groups. This methodology displays a wide tolerance toward functional groups, while also exhibiting good applicability across various skeletal structures of alkenols and amines.

show abstract

Biocatalytic reductive amination as a route to isotopically labelled amino acids suitable for analysis of large proteins by NMR

Abstract: We demonstrate an atom-efficient and easy to use H2-driven biocatalytic platform for the enantioselective synthesis of isotopically labelled amino acids for protein NMR studies.

Cited by 6 publications

References 45 publications

Robust Whole‐Cell‐Based Chemoenzymatic Synthesis of Site‐Selective Deuterated α‐Hydroxy Acids and α‐Amino Acids

Robust Whole‐Cell‐Based Chemoenzymatic Synthesis of Site‐Selective Deuterated α‐Hydroxy Acids and α‐Amino Acids

State‐of‐the‐Art Light‐Driven Hydrogen Generation from Formic Acid and Utilization in Enzymatic Hydrogenations

Multifunctionalization of Alkenyl Alcohols via a Sequential Relay Process

Contact Info

Product

Resources

About