23235-03-2Relevant articles and documents
DL-propargyl glycine intermediate and preparation method thereof, and propargyl glycine preparation method based on intermediate
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Page/Page column 6-8, (2020/06/20)
The invention relates to the field of amino acid preparation, in particular to a DL-propargyl glycine intermediate, a preparation method of the DL-propargyl glycine intermediate and a preparation method of propargyl glycine based on the DL-propargyl glycine intermediate. The preparation method of the DL-propargyl glycine intermediate comprises three steps of condensation, saponification and hydrolysis, and then corresponding derivatives can be obtained through a chemical resolution method and an enzyme resolution method respectively. According to the preparation method, the reaction time is shortened; the reaction is more thorough, thepreparation method of DL-propargyl glycine can be obtained through the reaction, two methods for preparing derivatives of D-propargyl glycine and L-propargylglycine are obtained at the same time, the prepared product is high in purity, secondary refining is not needed, the production cost is reduced, and industrial large-scale production is facilitated.
A Biocatalytic Route to Enantiomerically Pure Unsaturated α-H-α-Amino Acids
Wolf, Larissa B.,Sonke, Theo,Tjen, Kim C. M. F.,Kaptein, Bernard,Broxterman, Quirinus B.,Schoemaker, Hans E.,Rutjes, Floris P. J. T.
, p. 662 - 674 (2007/10/03)
A set of both enantiomeric forms of non-proteinogenic, unsaturated α-H-α-amino acids was efficiently synthesized using a biocatalytic pathway. This route involved the straightforward synthesis of the required unsaturated amino acid amides, followed by resolution with an aminopeptidase present in Pseudomonas putida ATCC 12633 and/or a genetically modified organism, leading to the (S)-acids and (R)-amides. Undesired amino acid racemase activity was identified in the wild-type strain, which was absent in the newly developed organism. The (R)-amides were hydrolyzed under mild conditions using an amidase present in whole cells from Rhodococcus erythropolis NCIMB 11540 to the (R)-acids. The viability of this procedure was demonstrated with the multi-gram synthesis of a variety of unsaturated amino acids in excellent enantiopurity.
Synthesis of the suicide substrate D-propargylglycine stereospecifically labelled with deuterium and investigation of its oxidation by D-amino acid oxidase
Church, Nicola J.,Young, Douglas W.
, p. 1475 - 1482 (2007/10/03)
Stereospecifically deuteriated samples of D-propargylglycine 1 have been prepared by reaction of the labelled Pmc-protected aziridine free acids 22 with a lithium acetylide followed by deprotection. These samples have been used to show that D-amino acid oxidase, in converting D-propargylglycine to the lactone 5, deprotonates C-3 in a non-stereospecific manner. This strongly supports the idea that non-enzymic deprotonation is a key step in the formation of this compound.
