Akabori amino-acid reaction

There are several Akabori amino acid reactions, which are named after Shirō Akabori (Japanese: 赤堀 四郎) (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.[1][2][3] This reaction is useful for preparing dichlorophthalimido derivatives of peptides for mass spectral analysis.[4]

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.[5][6] This process is conceptually similar to the Bouveault–Blanc reduction[7][8][9] except that it stops at the aldehyde stage rather than reducing the ester all the way to two alcohols.

See also

References
  1. S. Akabori (1931). "Amino Acids and Their Derivatives (I) Oxidative Decomposition of α-Amino Acids with Sugars. (I)". Nippon Kagaku Kaishi. 52: 606–610. doi:10.1246/nikkashi1921.52.606.
  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. 52 (12): 839–843. doi:10.1246/nikkashi1921.52.839.
  3. S. Akabori (1933). "Oxydativer Abbau von α-Amino-säuren durch Zucker". Chem. Ber. (in German). 66 (2): 143. doi:10.1002/cber.19330660213.
  4. "Akabori Amino Acid Reaction". Comprehensive Organic Name Reactions and Reagents. 8: 29–32. 2010. doi:10.1002/9780470638859.conrr008. ISBN 9780470638859.
  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.: 1695–1698. doi:10.1039/jr9550001695.
  6. A. Lawson (1956). "63. The reaction of cyanamide with α-amino-acetals and α-amino-aldehydes". J. Chem. Soc.: 307–310. doi:10.1039/jr9560000307.
  7. Bouveault, Louis; Blanc, Gustave Louis (1903). "Préparation des alcools primaires au moyen des acides correspondants" [Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. (in French). 136: 1676–1678.
  8. Bouveault, Louis; Blanc, Gustave Louis (1903). "Préparation des alcools primaires au moyen des acides correspondants" [Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. (in French). 137: 60–62.
  9. Bouveault, Louis; Blanc, Gustave Louis (1904). "Transformation des acides monobasiques saturés dans les alcools primaires correspondants" [Transforming saturated monobasic acids into the corresponding primary alcohols]. Bull. Soc. Chim. Fr. (in French). 31: 666–672.
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