Heyns rearrangement

The Heyns rearrangement is after its discoverer, the German chemist Kurt Heyns , called names reaction . It represents the initial phase of the Maillard reaction , in which the amino groups of the amino acids, as nucleophilic compounds, easily add to the carbonyl function of reducing sugars . If a ketose reacts , for example fructose , a rearrangement leads to an amino aldose, which is known as the Heyns compound (2-amino-2-deoxy-aldose). Since the addition of the amine and the addition of the proton to the intermediate amino enol can take place from two sides, a pair of enantiomers is formed .

The corresponding reaction of an aldose to aminoketosis is called the Amadori rearrangement .

Fructose ( 1 ) reacts with an amino acid with elimination of water to form an imine ( 3 ) and rearranges to the Heyns compound ( 5 ) via a 1,2-enaminol ( 4 ) .

Individual evidence

^ Hans-Dieter Belitz , Werner Grosch , Peter Schieberle : Textbook of food chemistry . 6th completely revised edition. Springer, Berlin / Heidelberg 2008, ISBN 978-3-540-73201-3 , doi : 10.1007 / 978-3-540-73202-0 .

[1] Hans-Dieter Belitz , Werner Grosch , Peter Schieberle : Textbook of food chemistry . 6th completely revised edition. Springer, Berlin / Heidelberg 2008, ISBN 978-3-540-73201-3 , doi : 10.1007 / 978-3-540-73202-0 .