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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
Author(s) -
Archer Robert M.,
Royer Sylvain F.,
Mahy William,
Winn Caroline L.,
Danson Michael J.,
Bull Steven D.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203489
Subject(s) - sulfolobus solfataricus , stereochemistry , chemistry , biochemistry , archaea , gene
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.