2611-88-3Relevant articles and documents
Enzymatic synthesis of N-methyl-L-phenylalanine by a novel enzyme, N-methyl-L-amino acid dehydrogenase, from Pseudomonas putida
Muramatsu, Hisashi,Mihara, Hisaaki,Kakutani, Ryo,Yasuda, Mari,Ueda, Makoto,Kurihara, Tatsuo,Esaki, Nobuyoshi
, p. 2841 - 2843 (2004)
An enzymatic system for the synthesis of N-methyl-l-phenylalanine from phenylpyruvic acid and methylamine with a novel enzyme, N-methyl-l-amino acid dehydrogenase from Pseudomonas putida ATCC12633, using NADP+ and glucose dehydrogenase from Bacillus subtilis as a co-factor-recycling system is described. Analysis of the product on a laboratory preparative scale process revealed N-methyl-l-phenylalanine in 98% yield and over 99% ee. N-Methyl-l-phenylalanine can be used as chiral building blocks for the synthesis of several products with pharmacological activity.
Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates
Bischoff, Amanda J.,Nelson, Brandon M.,Niemeyer, Zachary L.,Sigman, Matthew S.,Movassaghi, Mohammad
supporting information, p. 15539 - 15547 (2017/11/06)
The bis(pyridine)silver(I) permanganate promoted hydroxylation of diketopiperazines has served as a pivotal transformation in the synthesis of complex epipolythiodiketopiperazine alkaloids. This late-stage C-H oxidation chemistry is strategically critical to access N-acyl iminium ion intermediates necessary for nucleophilic thiolation of advanced diketopiperazines en route to potent epipolythiodiketopiperazine anticancer compounds. In this study, we develop an informative mathematical model using hydantoin derivatives as a training set of substrates by relating the relative rates of oxidation to various calculated molecular descriptors. The model prioritizes Hammett values and percent buried volume as key contributing factors in the hydantoin series while correctly predicting the experimentally observed oxidation sites in various complex diketopiperazine case studies. Thus, a method is presented by which to use simplified training molecules and resulting correlations to explain and predict reaction behavior for more complex substrates.
The facile production of N-methyl amino acids via oxazolidinones
Aurelio, Luigi,Brownlee, Robert T. C.,Hughes, Andrew B.,Sleebs, Brad E.
, p. 425 - 433 (2007/10/03)
A range of oxazolidinones derived from N-carbamoyl α-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most α-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl α-amino acids. CSIRO 2000.
