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Akabori amino-acid reaction

Type of amino acid reaction

Type of amino acid reaction

There are several Akabori amino acid reactions, which are named after Shirō Akabori (1900–1992), a Japanese chemist.

In the first reaction, an α-amino acid is oxidised and undergoes decarboxylation to give an aldehyde at the former α position by heating with oxygen in the presence of a reducing sugar. This reaction is useful for preparing dichlorophthalimido derivatives of peptides for mass spectral analysis.

:[[Image:Reacción de Akabori 1.png]]

In the second reaction, an α-amino acid, or an ester of it, is reduced by sodium amalgam and ethanolic HCl to give an α-amino aldehyde. This process is conceptually similar to the Bouveault–Blanc reduction except that it stops at the aldehyde stage rather than reducing the ester all the way to two alcohols.

:[[Image:Reacción de Akabori 2.png]]

References

References

  1. S. Akabori. (1931). "Amino Acids and Their Derivatives (I) Oxidative Decomposition of α-Amino Acids with Sugars. (I)". Nippon Kagaku Kaishi.
  2. S. Akabori. (1931). "Oxidative Degradation of α-Amino Acids with Sugars (II). On the Mechanisms of the Reaction. (Amino Acids and their Derivatives. II.)". Nippon Kagaku Kaishi.
  3. S. Akabori. (1933). "Oxydativer Abbau von α-Amino-säuren durch Zucker". [[Chem. Ber.]].
  4. (2010). "Comprehensive Organic Name Reactions and Reagents".
  5. A. Lawson, H.V. Motley. (1955). "2-Mercaptoglyoxalines. Part IX. The preparation of 1 : 5-disubstituted 2-mercaptoglyoxalines from α-amino-acids". [[J. Chem. Soc.]].
  6. A. Lawson. (1956). "63. The reaction of cyanamide with α-amino-acetals and α-amino-aldehydes". [[J. Chem. Soc.]].
  7. (1903). "Préparation des alcools primaires au moyen des acides correspondants". [[Compt. Rend.]].
  8. (1903). "Préparation des alcools primaires au moyen des acides correspondants". [[Compt. Rend.]].
  9. (1904). "Transformation des acides monobasiques saturés dans les alcools primaires correspondants". [[Bull. Soc. Chim. Fr.]].
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