135253-58-6Relevant articles and documents
3 - deoxy - D - monno -2 - octanone method for synthesizing sugar acid ammonium salt
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Paragraph 0057-0058, (2017/01/02)
The invention relates to a synthetic method of 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt. The synthetic method comprises the following steps: using D-sweet dew as a raw material and performing the reaction on D-sweet dew and 2,2-dimethoxy propane; protecting hydroxy at 2 and 3 positions and 5 and 6 positions by isopropylidene to obtain an intermediate in a formula I; performing the reaction on a product in the formula I and 2-dimethoxy phosphoroso-2-dimethyl tertiary butyl silica ethyl acetate in a formula II to obtain an intermediate in a formula III; removing a silicyl oxide protecting group in a product in the formula III to form intramolecular hemiketal so as to obtain an intermediate in a formula IV; performing the deprotection, saponification and ammonium salt formation reaction on a product in the formula IV to obtain the final product 3-deoxidized-D-sweet dew-2-octulosonic ammonium salt. The method has the advantages of low price of the raw material, easiness for obtaining the raw material, mild reaction condition, simplicity and convenience for operation, high safety, high route total yield, simplicity for purification treatment on the final product and stable quality of the final product, and thus, the synthetic method disclosed by the invention enables the total cost to be greatly reduced and is suitable for the requirements on large-scale industrial production.
Syntheses of 2-keto-3-deoxy-D-xylonate and 2-keto-3-deoxy-L-arabinonate as stereochemical probes for demonstrating the metabolic promiscuity of sulfolobus solfataricus towards D-xylose and L-arabinose
Archer, Robert M.,Royer, Sylvain F.,Mahy, William,Winn, Caroline L.,Danson, Michael J.,Bull, Steven D.
supporting information, p. 2895 - 2902 (2013/03/28)
Practical syntheses of 2-keto-3-deoxy-D-xylonate (D-KDX) and 2-keto-3-deoxy-L-arabinonate (L-KDA) that rely on reaction of the anion of ethyl 2-[(tert-butyldimethylsilyl)oxy]-2-(dimethoxy phosphoryl) acetate with enantiopure glyceraldehyde acetonide, followed by global deprotection of the resultant O-silyl-enol esters, have been developed. This has enabled us to confirm that a 2-keto-3-deoxy-D-gluconate aldolase from the archaeon Sulfolobus solfataricus demonstrates good activity for catalysis of the retro-aldol cleavage of both these enantiomers to afford pyruvate and glycolaldehyde. The stereochemical promiscuity of this aldolase towards these enantiomeric aldol substrates confirms that this organism employs a metabolically promiscuous pathway to catabolise the C5-sugars D-xylose and L-arabinose.
