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Strecker amino acid synthesis information


Strecker synthesis
Named after Adolph Strecker
Reaction type Substitution reaction
Identifiers
Organic Chemistry Portal strecker-synthesis
RSC ontology ID RXNO:0000207

The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with cyanide in the presence of ammonia. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid.[1][2] The method is used for the commercial production of racemic methionine from methional.[3]

Primary and secondary amines also give N-substituted amino acids. Likewise, the usage of ketones, instead of aldehydes, gives α,α-disubstituted amino acids.[4]

  1. ^ "dl-Alanine". Organic Syntheses. 9: 4. 1929. doi:10.15227/orgsyn.009.0004.
  2. ^ "a-Aminoisobutyric Acid". Organic Syntheses. 11: 4. 1931. doi:10.15227/orgsyn.011.0004.
  3. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  4. ^ Masumoto, Shuji; Usuda, Hiroyuki; Suzuki, Masato; Kanai, Motomu; Shibasaki, Masakatsu (May 2003). "Catalytic Enantioselective Strecker Reaction of Ketoimines". Journal of the American Chemical Society. 125 (19): 5634–5635. doi:10.1021/ja034980+. PMID 12733893.

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Strecker amino acid synthesis

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The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde...

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Cyanohydrin

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Cyanohydrins are intermediates in the Strecker amino acid synthesis. In aqueous acid, they are hydrolyzed to the α-hydroxy acid. Acetone cyanohydrin, (CH3)2C(OH)CN...

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Amino acid

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Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far...

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Glycine

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synthesis. The two main processes are amination of chloroacetic acid with ammonia, giving glycine and ammonium chloride, and the Strecker amino acid synthesis...

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Glycolic acid

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"glycolic acid" (acide glycolique). Glycolic acid was first prepared in 1851 by German chemist Adolph Strecker (1822–1871) and Russian chemist Nikolai Nikolaevich...

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Adolph Strecker

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Adolph Strecker (21 October 1822 – 7 November 1871) was a German chemist who is remembered primarily for his work with amino acids. Strecker was born...

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Sarcosine

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micromolar. Sarcosine can be produced industrially via the Strecker amino acid synthesis. A variety of surfactants are produced from sarcosine, for instance...

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Alanine

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first synthesized in 1850 when Adolph Strecker combined acetaldehyde and ammonia with hydrogen cyanide. The amino acid was named Alanin in German, in reference...

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Strecker

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Strecker amino acid synthesis, synthesize an amino acid from an aldehyde or ketone Strecker degradation, converts an α-amino acid into an aldehyde by...

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Ammonia

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carboxylic acids can be dehydrated to amides by heating to 150–200 °C as long as no thermally sensitive groups are present. Amino acids, using Strecker amino-acid...

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Ammonium cyanide

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aldehydes yield aminonitriles, as in the first step of the Strecker amino acid synthesis: NH4CN + CH3COCH3 → (CH3)2C(NH2)CN + H2O Ammonium cyanide is...

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List of organic reactions

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synthesis Stork acylation Stork enamine alkylation Strecker amino acid synthesis Strecker degradation Strecker sulfite alkylation Strecker synthesis Stereocontrolled...

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Sulfonate

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of a sulfonic acid. Its formula is R−S(=O)2−O−, containing the functional group −S(=O)2−O−, where R is typically an organyl group, amino group or a halogen...

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Maillard reaction

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(/maɪˈjɑːr/ my-YAR; French: [majaʁ]) is a chemical reaction between amino acids and reducing sugars to create melanoidins, the compounds which give browned...

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Hydrogen cyanide

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the monomer methyl methacrylate, from acetone, the amino acid methionine, via the Strecker synthesis, and the chelating agents EDTA and NTA. Via the hydrocyanation...

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Cyanosulfidic prebiotic synthesis

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reactions that produce individual components such as the Strecker synthesis of amino acids, the formose reaction for the production of sugars, and prebiotic...

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Phenylacetaldehyde

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hdl:2433/75368. Schonberg, Alexander; Radwan, Moubacher (1952). "The Strecker Degradation of α-Amino Acids". Chemical Reviews. 52 (2): 261–277. doi:10.1021/cr60156a002...

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Glycocyamine

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is released into the bloodstream. Guanidinoacetic acid was first prepared in 1861 by Adolph Strecker by reaction of cyanamide with glycine in aqueous solution:...

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Biocatalysis

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of racemic mixtures of synthetic amino acids. Many popular amino acid synthesis routes, such as the Strecker Synthesis, result in a mixture of R and S...

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Trisodium dicarboxymethyl alaninate

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acid, which is suspected of being carcinogenic Use of inexpensive raw materials, e.g. instead of pure L-alanine the raw mixture of Strecker synthesis...

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Carbonaceous chondrite

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formation of isovaline and other α-dialkyl amino acids in CM chondrites has been attributed to the Strecker synthesis which produces racemic mixtures of enantiomers...

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Lawsone

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Lawsone is hypothesized to undergo a reaction similar to Strecker synthesis in reactions with amino acids. Recent research has been conducted on lawsone's potential...

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