4658-69-9Relevant articles and documents
Stereoselective Synthesis of β-Branched Aromatic α-Amino Acids by Biocatalytic Dynamic Kinetic Resolution**
Chen, Jason S.,Li, Fuzhuo,Renata, Hans,Yang, Li-Cheng,Zhang, Jingyang
supporting information, p. 17680 - 17685 (2021/07/07)
β-Branched noncanonical amino acids are valuable molecules in modern drug development efforts. However, they are still challenging to prepare due to the need to set multiple stereocenters in a stereoselective fashion, and contemporary methods for the synthesis of such compounds often rely on the use of rare-transition-metal catalysts with designer ligands. Herein, we report a highly diastereo- and enantioselective biocatalytic transamination method to prepare a broad range of aromatic β-branched α-amino acids. Mechanistic studies show that the transformation proceeds through dynamic kinetic resolution that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction was applied to the synthesis of several sp3-rich cyclic fragments and the first total synthesis of jomthonic acid A.
Tricyclic derivative inhibitor as well as preparation method and applications thereof
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Paragraph 0431; 0439-0442, (2019/06/13)
The invention relates to a tricyclic derivative inhibitor as well as a preparation method and applications thereof, in particular to a compound shown in a general formula (I) in the description, a preparation method of the compound, pharmaceutical composi
Asymmetric C-Alkylation by the S-Adenosylmethionine-Dependent Methyltransferase SgvM
Sommer-Kamann, Christina,Fries, Alexander,Mordhorst, Silja,Andexer, Jennifer N.,Müller, Michael
supporting information, p. 4033 - 4036 (2017/03/27)
S-Adenosylmethionine-dependent methyltransferases (MTs) play a decisive role in the biosynthesis of natural products and in epigenetic processes. MTs catalyze the methylation of heteroatoms and even of carbon atoms, which, in many cases, is a challenging reaction in conventional synthesis. However, C-MTs are often highly substrate-specific. Herein, we show that SgvM from Streptomyces griseoviridis features an extended substrate scope with respect to the nucleophile as well as the electrophile. Aside from its physiological substrate 4-methyl-2-oxovalerate, SgvM catalyzes the (di)methylation of pyruvate, 2-oxobutyrate, 2-oxovalerate, and phenylpyruvate at the β-carbon atom. Chiral-phase HPLC analysis revealed that the methylation of 2-oxovalerate occurs with R selectivity while the ethylation of 2-oxobutyrate with S-adenosylethionine results in the S enantiomer of 3-methyl-2-oxovalerate. Thus SgvM could be a valuable tool for asymmetric biocatalytic C-alkylation reactions.
