文章基本信息

标题：Analogs of natural lipids. I. Synthesis and properties of tris-homoacyl derivatives of cyclopentane- 1,2,3-triols.
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作者：A J Hancock ; S M Greenwald ; H Z Sable 等
期刊名称：JLR Papers In Press
印刷版ISSN：0022-2275
电子版ISSN：1539-7262
出版年度：1975
卷号：16
期号：4
页码：300-307
语种：English
出版社：American Society for Biochemistry and Molecular Biology
摘要：A new series of analogs of triglycerides has been synthesized, in which the glycerol moiety is replaced by each of the three isomeric cyclopentanetriols. For each of the isomeric cyclopentane-1,2,3-triols (1,2,3/0; DL-1,2/3; and 1,3/2), the tris-homoacyl derivatives of octanoic, decanoic, lauric, myristic, palmitic, stearic, and dihydrosterculic acids were prepared by treatment of the respective triols with the appropriate acyl chloride in pyridine. The dihydrosterculates were prepared by fusing the triols with a mixture of the acyl anhydride and the corresponding potassium salt. It is proposed that because of restricted rotation of the carbon-carbon bonds the cyclopentanoid compounds are analogs of specific rotamers of triglycerides. Infrared spectra (KBr discs) obtained at room temperature show differences in crystal structure from series to series. A band near 720 cm-minus 1 (CH2 rock) is doubled in the 1,2,3/0 and 1,2/3 series and is single in the 1,3/2 series and the triglycerides. In each spectrum with a doublet at 720 cm-minus 1, a band near 1470 cm-minus 1 (CH2 bend) is doubled also. A strong band at 890 cm-minus 1 present in the triglyceride spectra is weak or missing from the spectra of the analogs. A band at 1418 cm-minus 1 (bending of CH2 adjacent to C equal to 0) present in the triglyceride spectra is demonstrable only in the 1,2,3/0 derivatives in comparison with the other three series. In all series the dihydrosterculates show a decrease in apparent polarity, relative to the stearates, significantly greater than expected from the introduction of an additional carbon atom. The potential utility of the analogs as probes of the effects of conformation on the physical properties and enzymatic susceptibility of glycerides is discussed.