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Volumn , Issue 40, 2005, Pages 5086-5087

One-step labelling of sphingolipids via a scrambling cross-metathesis reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; FLUORESCENT DYE; SPHINGOLIPID; SPHINGOSINE; SPHINGOSINE DERIVATIVE; SPHINGOSINE KINASE;

EID: 27644572136     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508132g     Document Type: Article
Times cited : (27)

References (16)
  • 6
    • 0034746687 scopus 로고    scopus 로고
    • For selected comprehensive reviews on the metathesis reaction, see: T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18;
    • (2001) Acc. Chem. Res. , vol.34 , pp. 18
    • Trnka, T.M.1    Grubbs, R.H.2
  • 9
    • 4444382295 scopus 로고    scopus 로고
    • Recently, two research groups published the total synthesis of ceramides via construction of the E-double bond in the sphingosine backbone via a cross-metathesis reaction of two terminal olefins: A. N. Rai and A. Basu, Org. Lett., 2004, 6, 2861;
    • (2004) Org. Lett. , vol.6 , pp. 2861
    • Rai, A.N.1    Basu, A.2
  • 12
    • 27644549960 scopus 로고    scopus 로고
    • note
    • nd generation Grubbs' catalyst (when C16-ceramide, sphingomyelin or biotinylated undecenyl residue was used, a few drops of dimethylformamide were added to dissolve the starting material). The mixture was heated to reflux for 2.5-4 h (even when unreacted starting material was still detectable, longer reaction time did not result in higher yields). The solvent was evaporated, and the residue was subjected to column chromatography. NBD-dimethylsphingosine was purified by chromatography on sephadex LH20 followed by preparative HPLC. NBD-sphingomyelin was purified by preparative HPLC.
  • 13
    • 27644599497 scopus 로고    scopus 로고
    • note
    • Prepared by reacting 10-undecenylamine and 4-chloro-7-nitrobenzofurazan.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.