Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4,5-trideuterio-d-erythro-sphingosine and 3-deuterio-d-erythro-sphingomyelin.
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.
Byun
Hoe-Sup
HS
Department of Chemistry and Biochemistry, Queens College of CUNY, Flushing, NY 11367-1597, USA.
Bittman
Robert
R
D000643:Ammonium Chloride / Q000737:chemistry; D001881:Borates / Q000737:chemistry; D002563:Cerium / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D041961:Deuterium Exchange Measurement; D005663:Furans / Q000737:chemistry; D010084:Oxidation-Reduction; D013109:Sphingomyelins / Q000138:chemical synthesis* / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
C556180:3,4,5-trideuterio-d-erythro-sphingosine; C556181:3-deuterio-d-erythro-sphingomyelin; D001881:Borates; D005663:Furans; D013109:Sphingomyelins; D000643:Ammonium Chloride; D002563:Cerium; C018674:tetrahydrofuran; C010634:sodium borate; D003903:Deuterium; D013110:Sphingosine