赤堀氨基酸反应

赤堀氨基酸反应（Akabori amino acid reaction）有两种：

  1. α-氨基酸在加热时被氧化性糖氧化。
  1. α-氨基酸及其酯类被钠汞齐在氯化氢的乙醇溶液中还原，生成 α-氨基醛。

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[具体情况如何？] of peptides for mass spectral analysis.[3]

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.

参见

参考资料

  1. ^ S. Akabori. Studies on amino acids and its derivatives. I. Oxidation of sugars for α-amino acids. J. Chetn. Soc. Japan, Pure Chem. Sect. 1931, 52: 606–810. 
  2. ^ S. Akabori. Oxydativer Abbau von α-Amino-säuren durch Zucker. Chem. Ber. 1933, 66 (2): 143. doi:10.1002/cber.19330660213 （德语）. 
  3. ^ Akabori Amino Acid Reaction. Comprehensive Organic Name Reactions and Reagents. 2010, 8: 29–32. doi:10.1002/9780470638859.conrr008. 
  4. ^ A. Lawson, H.V. Motley. 2-Mercaptoglyoxalines. Part IX. The preparation of 1 : 5-disubstituted 2-mercaptoglyoxalines from α-amino-acids. J. Chem. Soc. 1955: 1695. doi:10.1039/jr9550001695. 
  5. ^ A. Lawson. 63. The reaction of cyanamide with α-amino-acetals and α-amino-aldehydes. J. Chem. Soc. 1956: 307. doi:10.1039/jr9560000307. 
  6. ^ Bouveault, Louis; Blanc, Gustave Louis. Préparation des alcools primaires au moyen des acides correspondants [Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. 1903, 136: 1676–1678 [2019-03-08]. （原始内容存档于2019-03-27） （法语）. 
  7. ^ Bouveault, Louis; Blanc, Gustave Louis. Préparation des alcools primaires au moyen des acides correspondants [Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. 1903, 137: 60–62 （法语）. 
  8. ^ Bouveault, Louis; Blanc, Gustave Louis. Transformation des acides monobasiques saturés dans les alcools primaires correspondants [Transforming saturated monobasic acids into the corresponding primary alcohols]. Bull. Soc. Chim. Fr. 1904, 31: 666–672 [2019-03-08]. （原始内容存档于2019-11-15） （法语）. 

参考资料

  1. S. Akabori, J. Chem. Soc. Japan, 52, 606(1931); Ber, 66, 143,151(1933); J. Chem. Soc. Japan, 64, 608(1943)
  2. E. Takagi, et al., J. Pharm. Soc. Japan, 71, 648(1951); 72,812(1952)
  3. A. Lawson, H.V. Motley, J. Chem. Soc., 1955, 1695
  4. A. Lawson, J. Chem. Soc. 1956, 307
  5. Reference Source（页面存档备份，存于互联网档案馆）