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. Issue 8 (11th January 2013)

• Record Type: Journal Article
• Authors: Archer, Robert M.; Royer, Sylvain F.; Mahy, William; Winn, Caroline L.; Danson, Michael J.; Bull, Steven D.
• Is Part Of: Chemistry. Volume 19:Issue 8(2013)
• Page Start: 2895
• Page End: 2902
• Publication Date: 2013-01-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201203489
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Practical syntheses of 2‐keto‐3‐deoxy‐<sc>D</sc>‐xylonate (<sc>D</sc>‐KDX) and 2‐keto‐3‐deoxy‐<sc>L</sc>‐arabinonate (<sc>L</sc>‐KDA) that rely on reaction of the anion of ethyl 2‐[(<italic>tert</italic>‐butyldimethylsilyl)oxy]‐2‐(dimethoxy phosphoryl) acetate with enantiopure glyceraldehyde acetonide, followed by global deprotection of the resultant <italic>O</italic>‐silyl‐enol esters, have been developed. This has enabled us to confirm that a 2‐keto‐3‐deoxy‐<sc>D</sc>‐gluconate aldolase from the archaeon <italic>Sulfolobus solfataricus</italic> 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 <sc>D</sc>‐xylose and <sc>L</sc>‐arabinose.</p> </abstract>