2611-88-3Relevant academic research and scientific papers
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.
Preparation method of N-methylamino acid with optical configurations
-
Paragraph 0042; 0043, (2017/08/29)
The invention belongs to the field of medicine synthesis, relates to a preparation method of N-methylamino acid with optical configurations and in particular relates to a preparation method of N-methylamino acid with an R configuration and an S configuration. The preparation method is shown in the description. According to the preparation method provided by the invention, the configurations of reactants are transformed to obtain the N-methylamino acid with corresponding opposite configurations, and the preparation method is suitable for commercial scale production.
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.
Synthesis of optically active α-methylamino acids and amides through biocatalytic kinetic resolution of amides
Wang, Mei-Xiang,Liu, Jun,Wang, De-Xian,Zheng, Qi-Yu
, p. 2409 - 2416 (2007/10/03)
Catalyzed by Rhodococcus sp. AJ270, a nitrile hydratase and amidase containing microbial whole-cell catalyst, under very mild conditions, a number of racemic α-methylamino amides were resolved into the corresponding optically active (S)-(+)-α-methylamino acids and (R)-(-)-α- methylamino amides. The steric requirement of the amidase against α-amino phenylacetamides bearing methyl group(s) at α-amino nitrogen and/or α-carbon was also studied. Coupled with the chemical hydrolysis of amide, the biotransformation process provided a direct synthesis of α-methylamino acids in both enantiomeric forms from readily available racemic amides.
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.
Optical Resolution and Asymmetric Transformation of (RS)-N-Alkyl- and (RS)-N,N-Dialkyl-2-phenylglycines
Shiraiwa, Tadashi,Baba, Yoshihisa,Miyazaki, Hideya,Sakata, Shinji,Kawamura, Seiko,et al.
, p. 1430 - 1437 (2007/10/02)
Optical resolution of (RS)-N-methyl-2-phenylglycine and (RS)-N-ethyl-2-phenylglycine was carried out by using (1S)-10-camphorsulfonic acid as resolving agents, and that of (RS)-N-ethyl-N-methyl-2-phenylglycine by (R)- and (S)-1-phenylethylamine.Racemization rates of optically active Mpg, Epg, Emp, N,N-dimethyl-2-phenylglycine , and six α-amino acids were measured by heating in carboxylic acids.The electron-donating amino acid side chain and N-substituted alkyl group decreased therate to inhibit the formation of intermediary carbanions, whereas the electron-withdrawing side chain increased it.Asymmetric transformation of (RS)-Mpg, (RS)-Epg, and (RS)-Dmp was carried out on the basis of the results of optical resolution and racemization to give the corresponding enantiomers of approximately 100percent optical purities in over 70percent yield based on the sterting racemates.
NITROGEN ALKYLATION OF SCHIFF BASES AND AMIDINES AS A ROUTE TO N-ALKYL AMINO ACIDS
O'Donnell, Martin J.,Bruder, William A.,Daugherty, Byron W.,Liu, Deshan,Wojciechowski, Krzisztof
, p. 3651 - 3654 (2007/10/02)
Schiff base and amidine esters 3 are alkylated and then hydrolyzed to yield N-alkyl amino acids 4 in 41-75percent yield with hight to complete retention of optical activity.
