Strecker Degradation

Short description: Chemical reaction

The Strecker degradation is a chemical reaction which converts an α-amino acid into an aldehyde containing the side chain, by way of an imine intermediate. It is named after Adolph Strecker, a German chemist.

The original observation by Strecker involved the use of alloxan as the oxidant in the first step,^[1] followed by hydrolysis:

The reaction can take place using a variety of organic and inorganic reagents.^[2]

References

↑ Strecker, A (1862). "Notiz über eine eigenthümliche Oxydation durch Alloxan". Annalen der Chemie und Pharmacie 123 (2): 363–365. doi:10.1002/jlac.18621230312. http://babel.hathitrust.org/cgi/pt?id=mdp.39015026321938;view=1up;seq=373.
↑ Schönberg, Alexander; Moubacher, Radwan (1952). "The Strecker Degradation of α-Amino Acids". Chem. Rev. 50 (2): 261–277. doi:10.1021/cr60156a002.

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[1] Strecker, A (1862). "Notiz über eine eigenthümliche Oxydation durch Alloxan". Annalen der Chemie und Pharmacie 123 (2): 363–365. doi:10.1002/jlac.18621230312. http://babel.hathitrust.org/cgi/pt?id=mdp.39015026321938;view=1up;seq=373.

[2] Schönberg, Alexander; Moubacher, Radwan (1952). "The Strecker Degradation of α-Amino Acids". Chem. Rev. 50 (2): 261–277. doi:10.1021/cr60156a002.