Deuterium Studies Reveal a New Mechanism for the Formose Reaction Involving Hydride Shifts

In the formose reaction, formaldehyde is converted to glycolaldehyde, its dimer, under credible prebiotic conditions. Breslow proposed a mechanism for the process in 1959, but recent studies by Benner showed that it was wrong in detail. Our present studies clarify the mechanism, which involves the o...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-03, Vol.136 (10), p.3720-3723
Main Authors: Appayee, Chandrakumar, Breslow, Ronald
Format: Article
Language:English
Subjects:
Acetaldehyde - analogs & derivatives
Acetaldehyde - chemistry
Carbohydrates - chemistry
Deuterium - chemistry
Dimerization
Formaldehyde
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Summary:In the formose reaction, formaldehyde is converted to glycolaldehyde, its dimer, under credible prebiotic conditions. Breslow proposed a mechanism for the process in 1959, but recent studies by Benner showed that it was wrong in detail. Our present studies clarify the mechanism, which involves the original Breslow intermediates but some different connecting steps.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja410886c