ORGN 496 |
| Dihydroxyacetone phosphate (DHAP)-dependent aldolases have been widely used for organic synthesis of unnatural sugars or derivatives. Their strict substrate specificity and the high cost and instability of DHAP limited their practicality. Here we report that the DHAP-dependent aldolase L-rhamnulose-1-phosphate aldolase (RhaD) accepts dihydroxyacetone (DHA) as a substrate in the presence of borate buffer, presumably by reversible in situ formation of DHA borate ester. The reactions appear to be irreversible, with the products thermodynamically trapped as borate complexes. We have applied this discovery to develop a practical one-step synthesis of the non-caloric sweetener L-fructose. Short synthesis of a series of L-iminocyclitols, which are potential glycosidase inhibitors, will also be discussed.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
