209531-97-5Relevant academic research and scientific papers
Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor
Le Joubioux, Florian,Bridiau, Nicolas,Sanekli, Mehdi,Graber, Marianne,Maugard, Thierry
, p. 143 - 153 (2014)
Ceramides are spingolipid compounds that are very attractive as active components in both the pharmaceutical and the cosmetic industries. In this study, the synthesis of ceramide analogs, the so-called pseudo-ceramides, was carried out using for the first time a two-step continuous enzymatic process with immobilized Candida antarctica lipase B (Novozym435) in a packed-bed bioreactor. The first step involved the selective N-acylation of 3-amino-1,2-propanediol using stearic acid as the first acyl donor (i). This was followed by the selective O-acylation of the N-stearyl 3-amino-1,2-propanediol synthesized in the first step, with myristic acid as the second acyl donor, to produce a N,O-diacyl 3-amino-1,2-propanediol-type pseudo-ceramide, namely 1-O-myristyl,3-N-stearyl 3-amino-1,2-propanediol (ii). The process was first optimized by evaluating the influences of three factors: feed flow rate, quantity of biocatalyst and substrate concentration. Under optimal conditions an amide synthesis yield of 92% and a satisfying production rate of almost 3.15 mmol h-1gbiocatalyst-1(1128 mg h-1gbiocatalyst-1) were obtained. The second step, N-acyl 3-amino-1,2-propanediol O-acylation, was similarly optimized and in addition the effect of the substrate molar ratio was studied. Thus, an optimal pseudo-ceramide synthesis yield of 54% and a production rate of 0.46 mmol h-1gbiocatalyst-1(261 mg h-1gbiocatalyst-1) were reached at a 1:3 ratio of amide to fatty acid. In addition, it was demonstrated that this two-step process has great potential for the production of N,O-diacyl 3-amino-1,2-propanediol-type pseudo-ceramides on an industrial scale. It was shown in particular that Novozym435 could be used for more than 3 weeks without a drop in the yield during the first step of 3-amino-1,2-propanediol N-acylation, proving that this biocatalyst is very stable under these operational conditions. This factor would greatly reduce the need for biocatalyst replacement and significantly lower the associated cost.
Effects of Sulfur-Containing Analogues of Stearic Acid on Growth and Fatty Acid Biosynthesis in the Protozoan Crithidia fasciculata
Rahman, Mohammad D.,Ziering, David L.,Mannarelli, Sara J.,Swartz, Karen L.,Huang, Ded-Shih,Pascal, Robert A.
, p. 1656 - 1659 (1988)
A variety of analogues of stearic acid in which one of the methylene groups was replaced by a sulfur atom were examined as inhibitors of growth and fatty acid biosynthesis in the trypanosomatid protozoan Crithidia fasciculata.The 8-, 9-, 10-, and 11-thiastearic acids were found to suppress the synthesis of the cyclopropane-containing fatty acid dihydrosterculic acid (9,10-methyleneoctadecanoic acid) at micromolar concentrations in the growth medium, and all but the 9-thiastearate were found to inhibit the growth of the protozoa at comparable concentrations.The most potent inhibitor, 8-thiastearic acid (I50 for growth = 0.8 μM; I50 dihydrosterculate synthesis = 0.4 μM), was also observed to inhibit the synthesis of γ-linolenic acid at a similar concentration.The sulfoxide derivatives of the 9- and 10-thiastearates were found to have little effect on growth or fatty acid synthesis, and several long-chain amides of 3-amino-1,2-propanediol were found to have effects similar to those of the fatty acids from which they were derived.
Monoacylglycerols as transmembrane Cl- anion transporters
Bahmanjah, Soheila,Zhang, Ning,Davis, Jeffery T.
, p. 4432 - 4434 (2012)
We report that the amphiphilic natural product, monoacylglycerol 1, functions as a transmembrane Cl-/NO3- anion transporter. The 1,2-diol group is crucial for the transport function since diacylglycerol and triacylglycerol analogs are not anion transporters. Furthermore, adding another hydrogen bond donor to the glycerol head-group and perfluorination of the acyl tail gave synthetic analogs with improved Cl - membrane transport properties.
Modified oligonucleotides for telomerase inhibition
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Page/Page column 13, (2008/06/13)
Compounds comprising an oligonucleotide moiety covalently linked to a lipid moiety are disclosed. The oligonucleotide moiety comprises a sequence that is complementary to the RNA component of human telomerase. The compounds inhibit telomerase activity in
Structure-activity relationship for enhancement of paracellular permeability across Caco-2 cell monolayers by 3-alkylamido-2-alkoxypropylphosphocholines
Ouyang, Hui,Morris-Natschke, Susan L.,Ishaq, Khalid S.,Ward, Peter,Liu, Dongzhou,Leonard, Sarah,Thakker, Dhiren R.
, p. 2857 - 2866 (2007/10/03)
Paracellular permeability enhancers have been used to improve the oral bioavailability of hydrophilic drugs; however, the mechanism of action of many enhancers is poorly understood. In this study, highly potent enhancers of paracellular permeability were
Structure-activity relationships for enhancement of paracellular permeability by 2-alkoxy-3-alkylamidopropylphosphocholines across Caco-2 cell monolayers
Liu, Dong-Zhou,Morris-Natschke, Susan L.,Kucera, Louis S.,Ishaq, Khalid S.,Thakker, Dhiren R.
, p. 1169 - 1174 (2007/10/03)
The oral route is the preferred route of delivery for a large number of drug molecules. However, the intestinal epithelium presents a formidable barrier for delivery of drugs into systemic circulation. Phospholipids are among compounds that enhance the ab
Method of treating hepatitis virus infections
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, (2008/06/13)
A method of treating hepatitis virus infection is disclosed. The method comprising administering to a human subject in need of such treatment an effective hepatitis virus-combatting amount of an alkyl lipid or alkyl lipid derivative.
