Chemical and Functional Properties of Food Saccharides

OH
CH2OH CH2OH
OH
© 2004 by CRC Press LLC
O
OH
2.66 2.67 2.68
typical for reactions of common aldehydes do not form. Proportions of anomeric
mixtures of glycosylamines (2.71), which are formed instead, depend on the reaction
conditions and the structure of amine. In the reaction with bulky amines, reaction
of the equatorial isomer is strongly favored for steric reasons.
In aqueous solution, glycosylamines undergo mutarotation and hydrolyze. Formation
of an open-chain immonium structure was postulated in the intermediary
step followed by cyclization (mutarotation) or substitution (hydrolysis). There is a
strong link between these reactions and the Maillard reaction (see Chapter 18).
Several monographs 1–8 are recommended for further reading.
REFERENCES
H, OH + NH 2CONH 2
NHCONH2
+ H2O
1. Lehninger, A.L., Principles of Biochemistry, Worth Publishers, New York, 1982.
2. Armstrong, E.F., and Armstrong, K.F., The Glycosides, Longmans & Green, New
York, 1982.
3. The Carbohydrates, Chemistry and Biochemistry, Pipman, W. and Horton, D., Eds.,
Academic Press, New York, 1972.
4. Schers, H. and Bonn, G., Analytical Chemistry of Carbohydrates, Georg Thierne
Verlag, Stuttgart, 1998.
5. Driquez, H., and Thiem, J. (Eds), Glycoscience, Springer Verlag, Berlin, 1997.
6. Eliel, E.L., Wilen, S.H., and Mander, L.N., Stereochemistry of Organic Compounds,
Wiley–Interscience, New York, 1994.
7. Stoddart, J.F., Stereochemistry of Carbohydrates, Wiley–Interscience, New York,
1971.
8. Eliel, E.L. et al., Conformational Analysis, John Wiley & Sons, New York, 1965.
OH
OH
O
OH