Chemistry of a-aminonitriles. Aldomerization of glycolaldehyde phosphate to rac-hexose 2,4,6-triphosphates and (in presence of formaldehyde) rac-pentose 2,4-diphosphates: rac-allose 2,4,6-triphosphate and rac-ribose 2,4-diphosphate are the main reaction products

Glycoaldehyde phosphate aldomerizes in aq. NaOH to a product mixt. contg. the racemates of two diastereomeric tetrose 2,4-diphosphates and 8 hexose 2,4,5-triphosphates. The aldomerization of glycoaldehyde in the presence of formaldehyde is a variant of the formose reaction. It avoids the formation of complex formose product mixts., because C(2)-phosphorylated aldoses cannot undergo aldose-ketose tautomerization. This work, with its demonstration of an intrinsic kinetic preference for ribose 2,4-diphosphate and allose 2,4,5-triphosphate formation, adds a piece of factual chem. information to ongoing discussion about the origin of ribonucleic acids. [on SciFinder (R)]

Published in:
Helvetica Chimica Acta, 73, 5, 1410-68

 Record created 2006-02-27, last modified 2018-01-27

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