Synthesis and optical resolution of the neurotoxin 2‐amino‐3‐([15N]‐methylamino)propanoic acid (BMAA)
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Abstract The synthesis of 2‐amino‐3‐([ 15 N]‐methylamino)propanoic acid (synonyms, BMAA, β‐N‐methylamino‐alanine) from α‐acetamidoacrylic acid and [ 15 N]‐methylamine is described. Enantioselective hydrolysis of the acetamide group, mediated by the enzyme Acylase 1 (EC 3.5.1.14), yielded (R)‐BMAA and the (S)‐α‐acetamido derivative. Acid hydrolysis of the latter compound yielded (S)‐BMAA.Keywords:
Propanoic acid
Acetamide
Neurotoxin
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Alanine
Abstract 2-(4-Chlorophenyl)propanoic acid 1 is transformed to 2-(4-chloro-3-nitrophenyl) propanoic acid 2 (94% yield). Acid 2 can be converted to 2-(3-nitrophenyl)propanoic acid 3 (70% yield) or to 2-(3-aminophenyl) propanoic acid 4 (80% yield).
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Synthesis of propyl propanoic had been done. Propyl propanoic was synthesized via esterification of propanoic acid and 1-propanol in the presence of sulfuric acid catalyst with mole ratios of 4:3 to produce propyl propanoic. Structural characterization of products was done by means of IR, 1H-NMR, GC and GC-MS spectrometers. Esterification of propanoic acid with 1-propanol produced propyl propanoate in 72% yield.
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The title compound, C11H9NO4, was synthesized by mixing phthalic anhydride and (S)-2-aminopropanoic acid in acetic acid. The dihedral angle between the phthalimide ring system and the O3/O4/C9/C11 plane is 86.7 (3)°. The crystal structure is stabilized by weak O—H⋯O hydrogen bonds.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Infrared measurements of a series of complexes prepared with cobalt(II) phthalimide and some amines of the [Co(Phthalimide)2(amine)2or1] type have been made. The spectra confirm that both phthalimide ions and amine molecules are co-ordinated; they further suggest that the coordination of phthalimide is through the nitrogen.
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N- Methyl thiomethyl phthalimide (I) a new compound was obtained when phthalimide was refluxed with DMSO acetic anhydride reagent and DMSO alone at 180 o C. A different route for the synthesis of N- Hydroxy methylphthalilmide (II)with excellent yield has also been explored by this reaction. Key Words : DMSO, Acetic anhydride, Phthalimide, Methyl thiomethylation
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The crystal structure of the title compound, C(11)H(9)NO(4), consists of infinite one-dimensional polymeric chains due to inter-molecular O-H⋯O hydrogen bonds between the carboxyl-ate and carbonyl groups. The phthalimide ring system and the C-COO group are planar, with r.m.s. deviations of 0.0253 and 0.0067 Å, respectively, from their mean square planes and the dihedral angle between them is 66.41 (7)°. The mol-ecules are stabilized by C=O⋯π inter-actions and weak intra-molecular C-H⋯O hydrogen bonds.
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