Abstract
Deuteration at C-4 and C-5 of sphingosine was achieved via a hydrogen-deuterium exchange reaction of a β-ketophosphonate intermediate catalyzed by ND₄Cl in D₂O/tetrahydrofuran. To install deuterium at C-3 of sphingosine and sphingomyelin, sodium borodeuteride reduction/cerium(III) chloride reduction of an α,β-enone in perdeuteromethanol was used.
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Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Ammonium Chloride / chemistry
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Borates / chemistry
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Cerium / chemistry
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Deuterium / chemistry
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Deuterium Exchange Measurement
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Furans / chemistry
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Oxidation-Reduction
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Sphingomyelins / chemical synthesis*
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Sphingomyelins / chemistry
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Sphingosine / analogs & derivatives*
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Sphingosine / chemical synthesis
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Sphingosine / chemistry*
Substances
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3,4,5-trideuterio-d-erythro-sphingosine
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3-deuterio-d-erythro-sphingomyelin
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Borates
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Furans
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Sphingomyelins
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Ammonium Chloride
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Cerium
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tetrahydrofuran
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sodium borate
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Deuterium
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Sphingosine