- DL-propargyl glycine intermediate and preparation method thereof, and propargyl glycine preparation method based on intermediate
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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.
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Page/Page column 6-8
(2020/06/20)
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- A chiral amino acid preparation method
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The invention relates to a method for preparing a compound (OMLT-01). The method of the invention comprises the following steps: mixing the compound (OMLT-A) with liquor of sodium hydroxide in an amide solvent, cooling down to 0-10 DEG C, and dropwise add
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Paragraph 0042-0049
(2018/11/04)
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- An Alternative Scalable Process for the Synthesis of the Key Intermediate of Omarigliptin
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An alternative scalable process for the synthesis of the key intermediate of omarigliptin is described. The asymmetric synthesis relies on the initial diastereoselective alkylation and subsequent aluminum-catalyzed substrate-controlled Meerwein-Ponndorf-Verley reduction. A highly regioselective 5-exo-dig iodocyclization followed to afford 11b, which was then subjected to ring-opening cycloetherification to give product 1 with >99:1 dr and >99% ee in 31.2% overall yield in nine steps. This synthetic strategy has been successfully applied for multikilogram scale production.
- Sun, Guodong,Wei, Mingjie,Luo, Zhonghua,Liu, Yongjun,Chen, Zhijun,Wang, Zhongqing
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supporting information
p. 2074 - 2079
(2016/12/24)
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- Synthesis of ω-(hetero)arylalkynylated α-amino acid by sonogashira-type reactions in aqueous media
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(Chemical Equation Presented) Mild conditions are described that allow the palladium-catalyzed cross-coupling of Cα-alkynylated glycine with a wide variety of electron-rich and electron-poor aryl and heteroaryl halides in aqueous media.
- Brea, Roberto J.,Lopez-Deber, M. Pilar,Castedo, Luis,Granja, Juan R.
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p. 7870 - 7873
(2007/10/03)
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- A Biocatalytic Route to Enantiomerically Pure Unsaturated α-H-α-Amino Acids
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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.
- Wolf, Larissa B.,Sonke, Theo,Tjen, Kim C. M. F.,Kaptein, Bernard,Broxterman, Quirinus B.,Schoemaker, Hans E.,Rutjes, Floris P. J. T.
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p. 662 - 674
(2007/10/03)
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- Synthesis of the suicide substrate D-propargylglycine stereospecifically labelled with deuterium and investigation of its oxidation by D-amino acid oxidase
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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.
- Church, Nicola J.,Young, Douglas W.
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p. 1475 - 1482
(2007/10/03)
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- Pd-catalyzed cyclization reactions of acetylene-containing α-amino acids
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Acetylene-containing amino acids, obtained in enantiopure form via an enzymatic resolution process, serve as versatile intermediates in the synthesis of various highly functionalized heterocycles. The key transformations, intramolecular OC- and NC-bond formation, proceed via Pd- catalysis.
- Wolf, Larissa B.,Tjen, Kim C. M. F.,Rutjes, Floris P. J. T.,Hiemstra, Henk,Schoemaker, Hans E.
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p. 5081 - 5084
(2007/10/03)
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- Stereoselective, nonracemic synthesis of ω-borono-α-amino acids
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ω-Unsaturated α-amino acids are synthesized through condensation of allyl and propargyl bromides or of 9-bromoundecene with a Ni(II) complex of the Schiff base derived from glycine and BPB. Hydroboration with Ipc2BH followed by oxidation with acetaldehyde affords enantiomerically pure ω- borono-α-aminocarboxylic acids.
- Collet, Sylvain,Bauchat, Patrick,Danion-Bougot, Renee,Danion, Daniel
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p. 2121 - 2131
(2007/10/03)
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- Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent
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For the purpose of practical preparations of a variety of enantiomerically pure uncommon α-amino acids, alkylations of the chiral glycine equivalent 5, which possesses axially chiral binaphthol as an auxiliary, with several electrophiles were investigated. The alkylation proceeded smoothly in satisfactory chemical yield with high diastereo-selectivities to give protected α-amino acid derivatives. The free hydroxyl group of the auxiliary played an important role for the induction of diastereoselectivity. Using (S)-1,1'-binaphthalene-2,2'-diol as a chiral auxiliary, D-α-amino acid derivatives having the unnatural (R)-configuration were predominantly obtained. Some of the alkylated products were converted into free non- proteinogenic D-α-amino acids.
- Tanaka, Kiyoshi,Ahn, Mija,Watanabe, Yukari,Fuji, Kaoru
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p. 1771 - 1782
(2007/10/03)
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- Synthesis of Stereospecifically Labelled D-Prop-2-ynylglycine and Investigation of the Action of D-Amino Acid Oxidase
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Stereospecifically deuteriated samples of D-prop-2-ynylglycine 1 are synthesised by reaction of the labelled aziridines 13 with a carbon nucleophile followed by deprotection; incubation of these samples with D-amino acid oxidase indicates that, in formation of the lactone 5, deprotonation at C-3 is non-stereospecific, strongly supporting non-enzymatic deprotonation as a key step in the formation of this compound.
- Church, Nicola J.,Young, Douglas W.
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p. 943 - 944
(2007/10/02)
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- Chloroanalyland propargylglycyl dipeptides. Suicide substrate containing antibacterials
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A set of dipeptides containing the amino acid residues β-chloroalanine and propargylglycine, which are mechanism-based inactivators of purified microbial enzymes (alanine racemase and cystathionine γ-synthase, respectively), have been synthesized, and their antibacterial properties in vitro have been evaluated. Dipeptides containing a single β-chloro-L-alanyl residue (e.g., 3, 5, 9, and 10) or a single L-propargylglycyl residue (e.g., 12 and 15) are potent antibacterials. The in vitro antibiotic activity of β-chloro-L-alanine and of L-propargylglycine is increased as much as 4000-fold by incorporation of these residues into a dipeptide. Compounds that contain only a single enzyme-inactivating amino acid together with a second L-alanyl residue (3, 5, 12, and 15) have a restricted range of activity: of the species tested, only Streptococcus agalactiae, Staphylococcus aureus, and Staphylococcus epidermidis are sensitive. However, peptides that contain two suicide-substrate residues [e.g., β-Cl-LAla-β-Cl-LAla (8) or LppGly-LppGly (18)] are broad-spectrum antibacterials; as many as 12 different species of the 16 surveyed are sensitive. Dipeptides that contain an amino-terminal L-methionyl (9) or an L-norvalyl (10) residue and a carboxy-terminal β-chloro-L-alanyl unit are also effective against a large number of organisms; the spectra of activity are like those seen for 8 and 18. A 'mixed' dipeptide [β-Cl-LAla-LppGly, (21)] gives apparent synergism of antibiotic action of β-chloro-L-alanine and of L-propargylglycine when these two residues are incorporated into a single structure. Peptides of the D,D configuration (4, 6, 13, 16, and 20) and ones of L,D stereochemistry (e.g., 7) are not antibacterials. Peptides containing one (11 and 14) and two (17) D,L-propargylglycyl residues are unresolved sets of diastereomers; the mixtures of compounds are between two- and fourfold less active than the corresponding resolved L,L dipeptides (12, 15, and 18). These findings are consistent with a mechanism of action for these antibiotics involving stereoselective processing of the peptidyl unit in vivo.
- Cheung, Kam Sing,Wasserman, Steven A.,Dudek, Edward,Lerner, Stephen A.,Johnston, Michael
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p. 1733 - 1741
(2007/10/02)
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