The Isolation of Beef Sphingomyelins

Spencer, William A.; Schaffrin, R.

doi:10.1139/o64-178

Cited by 15 publications

(4 citation statements)

References 32 publications

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“…The sphingomyelin fraction from beef kidney was also purified over DEAE-cellulose. Hydrolysis gave a longchain base and a fatty acid fraction. The latter consisted of C 22:0, C 18:0, and C 16:0 in decreasing amounts (in agreement with previous data on sphingomyelin from beef kidney (Spencer and Schaffrin, 1964). The longchain base fraction, however, provided some unexpected results showing substantial differences, qualitative and quantitative (Table V), from the cerebroside composition.…”

supporting

confidence: 90%

Phytosphingosines and branched sphingosines in kidney

Carter¹,

Hirschberg²

1968

Biochemistry

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supporting

confidence: 90%

Phytosphingosines and branched sphingosines in kidney

Carter¹,

Hirschberg²

1968

Biochemistry

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“…Samples of the four diastereomeric, double lipid tail rhamnolipids (Rha-C10-C10) were hydrolyzed with 2 M NaOH to obtain the 3-hydroxydecanoic acid and esterified with BF 3 –MeOH, − Figure b. After isolation by flash column chromatography, optical rotation measurements of the four chloroform solutions were performed and compared with the literature values of d -3-hydroxy esters and acids of similar or longer chain length. ,,− As a control for the correlation of absolute configuration with the levorotary and dextrorotary attributes of the individual methyl (±)-3-hydroxydecanoate esters, we measured the optical rotation values of methyl ( R )-3-hydroxydecanoate ( 12 ) prepared in nominally high %ee (>99%) by a well described Noyori’s catalytic hydrogenation method ,− and methyl 3-( S )-hydroxydecanoate ester ( 8b′ ) with confirmed absolute configuration by Mosher’s ester analysis. All data pertaining to this analysis can be found in the Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Four Diastereomers of Monorhamnolipids

et al. 2017

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Rhamnolipids are amphiphilic glycolipids biosynthesized by bacteria that, due to their low toxicity and biodegradability, are potential replacements for synthetic surfactants. The previously limited access to pure materials at the gram scale has hindered extensive characterization of rhamnolipid structure-performance behavior. Here, we present an efficient and versatile synthetic methodology from which four diastereomers of the most common monorhamnolipid, α-rhamnopyranosyl-β-hydroxydecanoyl-β-hydroxydecanoate, are prepared and subsequently characterized. Exploration of their behavior at the air-water interface is reported and analyzed in terms of the absolute configuration of the lipid tail carbinols at pH 4.0 and 8.0. All diastereomers exhibit a minimum surface tension of about 28 mN/m without a significant difference between the protonated (nonionic) or deprotonated (anionic) states. At pH 4.0 (nonionic), all diastereomers have a critical micelle concentration (CMC) in the micromolar range. At pH 8.0 (anionic), CMC values for the (R,R), (S,S), and (S,R) diastereomers are approximately an order of magnitude higher than in their nonionic states, whereas the (R,S) diastereomer exhibits a CMC about five times larger.

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“…Citric acid was determined by the method of Saffran and Denstedt [13], modified by Lowenstein and Spencer [14].…”

Section: Methodsmentioning

confidence: 99%