122885-25-0Relevant academic research and scientific papers
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.
Selective azetidine and tetrahydropyridine formation via Pd-catalyzed cyclizations of allene-substituted amines and amino acids
Rutjes, Floris P. J. T.,Tjen, Kim C. M. F.,Wolf, Larissa B.,Karstens, Willem F. J.,Schoemaker, Hans E.,Hiemstra, Henk
, p. 717 - 720 (2008/02/12)
Formula presented By choosing the right substituents either highly functionalized unusual four-membered ring amino acids or the isomeric pipecolic acid derivatives are obtained in enantiomerically pure form. Starting material is a linear allene-containing amino acid that has been resolved via biocatalysis.
Palladium-Catalyzed Synthesis of γ-Allenic α-Amino Acids
Cazes, Bernard,Djahanbini, Dariouche,Gore, Jacques,Genet, Jean-Piere,Gaudin, Jean-Marc
, p. 983 - 985 (2007/10/02)
γ-Allenic α-amino acids can be obtained by a three-step sequence from the phosphates of α-allenic alcohols: i) palladium-catalyzed alkylation of a Schiff base derived from glycine ester by these phosphates, ii) acidic hydrolysis of the imine functionality, and iii) saponification of the resulting amino esters.
