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Akabori amino-acid reaction

Lianyungang Klinechem Co.,Ltd | Updated: Nov 28, 2018

There are several Akabori amino acid reactions, which are named after Shirō Akabori (jap. 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] This reaction is useful for preparing dichlorophthalimido derivatives[how?] of peptides for mass spectral analysis.[3]

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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.[4][5] This process is conceptually similar to the Bouveault–Blanc reduction[6][7][8] except that it stops at the aldehyde stage rather than reducing the ester all the way to two alcohols.

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See also

Maillard reaction

References

1.     Jump up^ S. Akabori (1931). "Studies on amino acids and its derivatives. I. Oxidation of sugars for α-amino acids". J. Chetn. Soc. Japan, Pure Chem. Sect. 52: 606–810.

2.     Jump up^ S. Akabori (1933). "Oxydativer Abbau von α-Amino-säuren durch Zucker". Chem. Ber. (in German). 66 (2): 143. doi:10.1002/cber.19330660213.

3.     Jump up^ "Akabori Amino Acid Reaction". Comprehensive Organic Name Reactions and Reagents. 8: 29–32. 2010. doi:10.1002/9780470638859.conrr008.

4.     Jump up^ 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. doi:10.1039/jr9550001695.

5.     Jump up^ A. Lawson (1956). "63. The reaction of cyanamide with α-amino-acetals and α-amino-aldehydes". J. Chem. Soc.: 307. doi:10.1039/jr9560000307.

6.     Jump up^ 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.

7.     Jump up^ 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.

8.     Jump up^ 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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