✍ Scribed by Jörn Piel; Wilhelm Boland
No coin nor oath required. For personal study only.
An efficient and versatilesynthesisof ldeoxy-[4,4-2H2] -L2-xyhdose lb (= ldeoxy-[4,4-2H2] -othreopentuloae) fromdimethyl2,3-O-isopropyli&ne-mtartrate in 31Y.overallyield is deaeribed. The synthetic protocolallows a flexible adaptationto otherIabellingpatternsand isotopes.Labelledldeoxy-xyhrkraeis of bighvahreas a metabolicprobein biosyntheticstudiestowardsterpenoidsandprenylatedcompoundsfollowing theRohmerpathway.O 1997Publishedby ElsevierScienceLtd.
l-Deoxy-D-xyhdose la, first isolatedin 1976fromStre@mnyces hygroscopicus,' and its 5-phosphate2 representimportantintermediateswithinseveralbiochemical pathwaysof pro-and eucaryotes.In bacterif or exampleE. coli, la is incorporatedintothe thiazolenucleusof thiamin(vitaminB1)2and fromthere into pyridoxine(vitaminBC).3After the recent discoveryof a novel, mevalonate-independent pathwaytowards terpenoidsby Rohmeret al., la has gainedmuchattentionas an alternateprecursorof isopentenyldiphosphate(IPP)anddimethylallyl diphosphate(DMAP),the two principal buildingblocksof allterpenoids.&s
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