Document Detail

An efficient route to N-palmitoyl-D-erythro-sphingomyelin and its 13C-labeled derivatives.
MedLine Citation:
PMID:  8118917     Owner:  NLM     Status:  MEDLINE    
We describe here a practical and efficient route to a homogeneous N-palmitoyl-D-erythro-sphingomyelin and its 13C-labeled derivatives. (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octad ecene-1-ol 1 was converted to the sphingosine equivalent 2 by treatment with triphenylphosphine and water. Amine 2 was then coupled with palmitic acid, affording the ceramide derivative 3a. In the following two reactions the phosphorylcholine functional group was generated by using 2-chloro-2-oxo-1,3,2-dioxaphospholane and trimethylamine, respectively. The final deprotection of the secondary hydroxyl group in 5a produced the desired N-palmitoyl-D-erythro-sphingomyelin 6a. The overall yield of this five-step synthesis is 43%. The melting point, 213-215 degrees C, the specific rotation, [alpha]20D = +6.8 (c = 1.3, CH2Cl2/MeOH 1:1) and 1H- and 13C-NMR data indicate that the synthetic sphingomyelin is enantiomerically pure. The 13C-labeled derivatives 6b, 6c and 6d were synthesized by employing the same scheme.
Z Dong; J A Butcher
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  66     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  1993 Nov 
Date Detail:
Created Date:  1994-04-06     Completed Date:  1994-04-06     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  IRELAND    
Other Details:
Languages:  eng     Pagination:  41-6     Citation Subset:  IM    
Clippinger Laboratories, Department of Chemistry, Ohio University, Athens 45701.
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MeSH Terms
Carbon Isotopes
Indicators and Reagents
Isotope Labeling / methods
Magnetic Resonance Spectroscopy / methods
Molecular Structure
Optical Rotation
Sphingomyelins / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Carbon Isotopes; 0/Indicators and Reagents; 0/Sphingomyelins; 0/palmitoylsphingomyelin

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