ISSN:
0170-2041
Keywords:
L-Xylose
;
2-Deoxy-L-xylo-hexose
;
Enzymatic syntheses
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Chemo-Enzymatic Synthesis of Carbohydrates: The Preparation of L-Xylose and 2-Deoxy-L-xylo-hexoseA synthetic approach to L-xylose (6) and 2-deoxy-L-xylo-hexose (8) has been developed. The strategy utilizes achiral starting materials and employs two enzymatic reactions to introduce the desired chiral centers. Rabbit muscle aldolase (RAMA)-catalyzed condensation of (3-phenylthio)propanal (1) with dihydroxyacetone phosphate (DHAP) affords the C-6 skeleton 2 with D-threo configuration between C-3 and C-4. Diastereoselective reduction of 2 with sorbitol dehydrogenase (SDH) introduces the final stereocenter of the tetrahydroxy derivative 3. After oxidation of sulfide 3 to the corresponding diastereotopic sulfoxides 4, L-xylose (6) is obtained by thermal elimination of phenylsulfenic acid followed by ozonolysis. 2-Deoxy-L-xylo-hexose (8) is yielded from 4 by a Pummerer rearrangement and subsequent reductive deprotection (DI-BAL-H) of the rearrangement product 7.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199219920119
Permalink
