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Volumn 64, Issue 21, 1999, Pages 7727-7737

A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; DIACYLGLYCEROL; GLYCERIC ACID; OXYGEN; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; SULFUR; TRIMETHYLAMINE;

EID: 0032741250     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990414e     Document Type: Article
Times cited : (42)

References (72)
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    • 4 could also be accomplished in high yield, substantial losses occurred on isolation of the product, most likely as a result of chelation of aluminum by the bis-diol function of compound 6.
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    • 19-21 resulted in lower yields as well: compound 7b was obtained in 43% along with the sn-2-regioisomer (10%) and the 1,2-diacyl product (8.1%), compared to the 71% yield obtained under the reaction conditions shown in Scheme 1.
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    • note
    • We observed no significant acyl migration during the workup and subsequent chromatography.
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    • It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
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    • (b) The absorption spectrum of the dansyl chromophore overlaps with the emission spectra of β-naphthylacetyl group. The N-methylanthranoyl fluorophore also absorbs at the emission maximum of the β-naphthylacetyl sprctrum (see the Experimental Section).
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    • The p-nitrophenyl eater of 12-TCBOC-aminolauric acid was prepared in reaction between 12-TCBOC-aminolauric acid and p-nitrophenol using DCC as coupling agent.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.