541-15-1Relevant academic research and scientific papers
Preparation method of L-carnitine
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Paragraph 0034; -0035; 0038-0040; 0051, (2021/12/07)
The invention relates to the technical field of organic synthesis, in particular to a preparation method of L-carnitine, which comprises the following steps: by taking R-4-chloro-3-hydroxybutyrate as a raw material, carrying out catalytic cyclization under an alkaline condition to generate (2R)-2-ethylene oxide ethyl acetate, and carrying out ring-opening reaction with trimethylamine to obtain the L-carnitine. According to the invention, the technical scheme of first cyclization and then ring opening is adopted, so that the step of removing halide ions in ion exchange resin is avoided, byproducts such as sodium chloride and the like are convenient to remove, and the production cost is reduced; the method is simple to operate, low in production cost, high in target product purity, high in yield and suitable for being applied to industrial production.
Shedding light on the mitochondrial matrix through a functional membrane transporter
Blázquez-Moraleja, Alberto,Sáenz-De-Santa María, Ines,Chiara, María D.,álvarez-Fernández, Delia,García-Moreno, Inmaculada,Prieto-Montero, Ruth,Martínez-Martínez, Virginia,López Arbeloa, I?igo,Chiara, Jose Luis
, p. 1052 - 1065 (2020/02/11)
The first fluorescent probes that are actively channeled into the mitochondrial matrix by a specific mitochondrial membrane transporter in living cells have been developed. The new functional probes (BCT) have a minimalist structural design based on the highly efficient and photostable BODIPY chromophore and carnitine as a biotargeting element. Both units are orthogonally bonded through the common boron atom, thus avoiding the use of complex polyatomic connectors. In contrast to known mitochondria-specific dyes, BCTs selectively label these organelles regardless of their transmembrane potential and in an enantioselective way. The obtained experimental evidence supports carnitine-acylcarnitine translocase (CACT) as the key transporter protein for BCTs, which behave therefore as acylcarnitine biomimetics. This simple structural design can be readily extended to other structurally diverse starting F-BODIPYs to obtain BCTs with varied emission wavelengths along the visible and NIR spectral regions and with multifunctional capabilities. BCTs are the first fluorescent derivatives of carnitine to be used in cell microscopy and stand as promising research tools to explore the role of the carnitine shuttle system in cancer and metabolic diseases. Extension of this approach to other small-molecule mitochondrial transporters is envisaged.
Micro-reaction continuous flow synthesis method of levocarnitine
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Paragraph 0042-0064, (2020/09/08)
The invention provides a micro-reaction continuous flow synthesis method of levocarnitine. An existing preparation method has the defects of complicated operation, long reaction time, low yield and the like. According to the method, (R)-4-halogenated-3-hydroxybutyrate and trimethylamine are continuously subjected to quaternization and hydrolysis reaction in a micro-channel reactor in the presenceof an alkali to prepare the levocarnitine. The reaction time of the method is only several minutes, the yield is high, the technological process is easy and convenient to operate, and industrial production is easy.
A New Microbial Pathway for Organophosphonate Degradation Catalyzed by Two Previously Misannotated Non-Heme-Iron Oxygenases
Rajakovich, Lauren J.,Pandelia, Maria-Eirini,Mitchell, Andrew J.,Chang, Wei-Chen,Zhang, Bo,Boal, Amie K.,Krebs, Carsten,Bollinger, J. Martin
, p. 1627 - 1647 (2019/03/19)
The assignment of biochemical functions to hypothetical proteins is challenged by functional diversification within many protein structural superfamilies. This diversification, which is particularly common for metalloenzymes, renders functional annotations that are founded solely on sequence and domain similarities unreliable and often erroneous. Definitive biochemical characterization to delineate functional subgroups within these superfamilies will aid in improving bioinformatic approaches for functional annotation. We describe here the structural and functional characterization of two non-heme-iron oxygenases, TmpA and TmpB, which are encoded by a genomically clustered pair of genes found in more than 350 species of bacteria. TmpA and TmpB are functional homologues of a pair of enzymes (PhnY and PhnZ) that degrade 2-aminoethylphosphonate but instead act on its naturally occurring, quaternary ammonium analogue, 2-(trimethylammonio)ethylphosphonate (TMAEP). TmpA, an iron(II)- and 2-(oxo)glutarate-dependent oxygenase misannotated as a γ-butyrobetaine (γbb) hydroxylase, shows no activity toward γbb but efficiently hydroxylates TMAEP. The product, (R)-1-hydroxy-2-(trimethylammonio)ethylphosphonate [(R)-OH-TMAEP], then serves as the substrate for the second enzyme, TmpB. By contrast to its purported phosphohydrolytic activity, TmpB is an HD-domain oxygenase that uses a mixed-valent diiron cofactor to enact oxidative cleavage of the C-P bond of its substrate, yielding glycine betaine and phosphate. The high specificities of TmpA and TmpB for their N-trimethylated substrates suggest that they have evolved specifically to degrade TMAEP, which was not previously known to be subject to microbial catabolism. This study thus adds to the growing list of known pathways through which microbes break down organophosphonates to harvest phosphorus, carbon, and nitrogen in nutrient-limited niches.
Preparation method for synthesizing L-carnitine by using R-(-)-epichlorohydrin as starting material
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Paragraph 0078-0093, (2019/11/12)
The invention discloses a preparation method for synthesizing L-carnitine by using R-(-)-epichlorohydrin as a starting material, and belongs to the field of medicinal chemistry. The method comprises the steps: using R-(-)-epoxychlorohydrin and hydrocyanic acid as starting materials, performing a reaction for synthesis of R-4-chloro-3-hydroxybutyronitrile under the action of a basic catalyst, thensynthesizing L-carnitine hydrochloride through two routes, purifying the L-carnitine hydrochloride prepared through the two routes further through resin so as to remove chloride ions, and preparing the final product L-carnitine. The two process routes are simple, the reaction conditions are mild, the operation is simple and feasible, and industrial production is convenient; the whole process is green and environmentally friendly, the reaction yield is high, three waste is little, no sodium cyanide is used, and no solid waste sodium salt is generated; and the hydrolysis by-product ammonium chloride has good quality, and can be sold as a by-product, and great economic benefits and market competitiveness are achieved.
Asymmetric synthesis method of L-carnitine
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Page/Page column 4-9, (2019/12/02)
The invention relates to an asymmetric synthesis method of L-carnitine. Acetyl chloride (II) generates ketene in situ at a low temperature under the catalysis of organic base, the ketene and 2-chloroacetaldehyde (I) are directly subjected to an asymmetric intermolecular [2+2] cycloaddition reaction without separation in the presence of Lewis acid and a chiral catalyst to obtain chiral lactone, andlactone (IV) is reacted with a trimethylamine solution to obtain L-carnitine with high enantioselectivity. The synthetic method is simple, the yield of asymmetric catalytic products is high, the enantioselectivity of lactone products is 95% or above, conditions are mild, operation is easy, the production cost is low, and the method can be used for industrial production.
Synthesis method of quaternary amine inner salt
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Paragraph 0080; 0081, (2019/01/14)
The invention discloses a synthesis method of quaternary amine inner salt. The synthesis method comprises the following steps: (a) reduction reaction: taking a compound having a structure shown as theformula I as a raw material, carrying out a reduction reaction among the compound, an apoenzyme, a dehydrogenase and a coenzyme in monosaccharide within a certain pH range, removing enzymes with active carbon and performing rectification, so as to obtain a reduced product shown in the original specification, wherein X represents one of chlorine, bromine and iodine in halogens, and R represents one of a saturated alkyl or an unsaturated alkyl; (b) synthesis of the quaternary amine inner salt: carrying out a reaction between an obtained product and trimethylamine under a strong base condition to obtain quaternary amine hydrochloride, exchanging the quaternary amine hydrochloride in ion exchange resin to remove halide ions, performing concentration and refining a concentrated product with alcohol and acetone, so as to obtain the quaternary amine inner salt. The synthesis method has the advantages of being high in yield in each step, simple to operate and mild in reaction conditions, effectively removing enzyme residues by introducing a chiral structure with a high-selectivity enzymatic method, avoiding a reagent with high toxicity and high pollution by utilizing renewable resin for desalting, obtaining the high-purity product, being suitable for industrial production and the like.
METHODS AND COMPOSITIONS RELATING TO CARNITINE- DERIVED MATERIALS
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, (2019/01/05)
Zwitterionic monomers, camitine-derived zwitterionic polymers, carnitine ester cationic monomers, carnitine ester cationic polymers, conjugate compositions including a carnitine-derived zwitterionic polymer, and related compositions' and methods are provided which have various uses including as coatings, pharmaceuticals, diagnostics, encapsulation materials, and antifouling materials, among other utilities.
A low-cost high-safety L - carnitine preparation method (by machine translation)
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Paragraph 0023; 0025; 0030; 0031; 0041; 0043; 0045, (2018/07/30)
The invention relates to a kind of vitamin nutrient preparation method, in particular to a low-cost high-safety L - carnitine preparation method. It is to solve the problems of the prior art L - carnitine preparation of unstable product quality, the use of highly toxic chemicals cyanide, in production had a certain amount of risk, and the production cost is higher. The present invention is added in the high-pressure reactor chloro acetyl ethyl acetate and anhydrous ethanol, access trimethylamine gas, and then adding the compound (III), catalyst and methanol times, stir for three times after hydrogen replacement, recovery of catalyst, filtering to obtain the compound (II), in the reactor, (II) compound is added and the sodium hydroxide solution, then stirring under heating to reflux the reaction, after the reaction, to obtain the L - carnitine crude alkali solution, through the cation exchange resin treatment to remove impurities, to obtain an aqueous solution of L - carnitine, concentrated, vacuum drying to obtain L - carnitine (I) works. (by machine translation)
Novel method for preparing L-carnitine
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Paragraph 0021, (2017/08/27)
The invention discloses a novel method for preparing L-carnitine and belongs to the technical field of medication chemistry. The method disclosed by the invention comprises the following steps: reacting quinine I and trimethylchlorosilane, thereby obtaining a quinine derivative II; reacting the quinine derivative II with racemic epoxy chloropropane, thereby obtaining quinine derivative quaternary ammonium salt III; reacting the quinine derivative quaternary ammonium salt III with a cyanide inorganic salt, and performing chiral ring opening to generate (R)-2-hydroxynitrile quaternary ammonium salt IV; carrying out an ion exchange reaction between the (R)-2-hydroxynitrile quaternary ammonium salt IV and trimethylamine, thereby obtaining (R)-2-hydroxynitrile trimethylamine salt, performing acidic hydrolysis, and performing ion exchange desalination, thereby obtaining the L-carnitine. The method provided by the invention is simple and feasible, the yield is greatly improved, and residues of heavy metal ions are avoided.
