7145-33-7

Upstream product

• 100-39-0 benzyl bromide 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 112-76-5 Stearoyl chloride 
• 98238-47-2 4-((benzyloxy)methyl)-1,3-dioxolane 
• 57-11-4 stearic acid 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 14347-83-2 (R)-2,2-dimethyl-4-benzoxymethyl-1,3-dioxolane 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 
• 100-44-7 benzyl chloride 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 638-08-4 stearic anhydride 
• 4145-51-1 3-O-Benzyl-1-O-octadecanoyl-sn-glycerin 
• 111-63-7 vinyl stearate 

Relevant academic research and scientific papers

Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids

The stereospecific structure of triacylglycerols (TAGs) affects the bioavailability of fatty acids. Lack of enantiopure reference compounds and effective enantiospecific methods have hindered the stereospecific analysis of individual TAGs. Twelve novel enantiostructured AAB-type TAGs were synthesized containing one of the three n-3 polyunsaturated fatty acid: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), or docosahexaenoic acid (DHA) in sn-1 or sn-3 position. These compounds formed six enantiomer pairs, which were separated with recycling high-performance liquid chromatography using chiral columns and UV detection. The chromatographic retention behavior of the enantiomers and the stereospecific elution order were studied. The enantiomer with an n-3 PUFA in the sn-1 position eluted faster than the enantiomer with the n-3 PUFA in the sn-3 position, regardless of the carbon chain length and number of double bonds of the PUFA. TAG enantiomers containing DHA exhibited highly different retention on the chiral column and were separated after the first column, whereas recycling was needed to separate the enantiomer pairs containing ALA or EPA. The system using two identical columns and one mobile phase, without sample derivatization, proved to be very effective also for peak purity assessment, confirming the enantiopurity of the synthesized structured TAGs being higher than 98 percent (96 percent ee).

Preparation, supramolecular aggregation and immunological activity of the bona fide vaccine adjuvant sulfavant S

In aqueous conditions, amphiphilic bioactive molecules are able to form self-assembled colloidal structures modifying their biological activity. This behavior is generally neglected in preclinical studies, despite its impact on pharmacological development. In this regard, a significative example is represented by a new class of amphiphilic marine-inspired vaccine adjuvants, collectively named Sulfavants, based on the β-sulfoquinovosyl-diacylglyceride skeleton. The family includes the lead product Sulfavant A (1) and two epimers, Sulfavant R (2) and Sulfavant S (3), differing only for the stereochemistry at C-2 of glycerol. The three compounds showed a significant difference in immunological potency, presumably correlated with change of the aggregates in water. Here, a new synthesis of diastereopure 3 was achieved, and the study of the immunomodulatory behavior of mixtures of 2/3 proved that the bizarre in vitro response to 1–3 effectively depends on the supramolecular aggregation states, likely affecting the bioavailability of agonists that can effectively interact with the cellular targets. The evidence obtained with the mixture of pure Sulfavant R (2) and Sulfavant S (3) proves, for the first time, that supramolecular organization of a mixture of active epimers in aqueous solution can bias evaluation of their biological and pharmacological potential.

Synthesis process of novel compound phosphatidyl 3-hydroxypropionitrile

The invention relates to a synthesis process of a novel compound phosphatidyl 3-hydroxypropionitrile. The synthesis process comprises the following steps: using acetone glycerol as a starting material; protecting exposed hydroxyl with benzyl; removing a ketal protecting group to obtain two exposed hydroxyls; then, esterifying with stearic acid; removing benzyl protection to obtain the exposed hydroxyl; reacting with a chlorophosphine compound to obtain a phosphine oxide compound; oxidizing to obtain phosphine oxide; and removing one molecular propyl nitrile to obtain a final product phosphatidyl 3-hydroxypropionitrile.

COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS

This disclosure provides improved lipid-based compositions, including lipid nanoparticle compositions, and methods of use thereof for delivering agents in vivo including nucleic acids and proteins. These compositions are not subject to accelerated blood clearance and they have an improved toxicity profile in vivo.

Synthesis of unsaturated phosphatidylinositol 4-phosphates and the effects of substrate unsaturation on SopB phosphatase activity

In this paper evidence is presented that the fatty acid component of an inositide substrate affects the kinetic parameters of the lipid phosphatase Salmonella Outer Protein B (SopB). A succinct route was used to prepare the naturally occurring enantiomer of phosphatidylinositol 4-phosphate (PI-4-P) with saturated, as well as singly, triply and quadruply unsaturated, fatty acid esters, in four stages: (1) The enantiomers of 2,3:5,6-O-dicyclohexylidene-myo-inositol were resolved by crystallisation of their di(acetylmandelate) diastereoisomers. (2) The resulting diol was phosphorylated regio-selectively exclusively on the 1-O using the new reagent tri(2-cyanoethyl)phosphite. (3) With the 4-OH still unprotected, the glyceride was coupled using phosphate tri-ester methodology. (4) A final phosphorylation of the 4-O, followed by global deprotection under basic then acidic conditions, provided PI-4-P bearing a range of sn-1-stearoyl, sn-2-stearoyl, -oleoyl, -γ-linolenoyl and arachidonoyl, glycerides. Enzymological studies showed that the introduction of cis-unsaturated bonds has a measurable influence on the activity (relative Vmax) of SopB. Mono-unsaturated PI-4-P exhibited a five-fold higher activity, with a two-fold higher KM, over the saturated substrate, when presented in DOPC vesicles. Poly-unsaturated PI-4-P showed little further change with respect to the singly unsaturated species. This result, coupled with our previous report that saturated PI-4-P has much higher stored curvature elastic stress than PI, supports the hypothesis that the activity of inositide phosphatase SopB has a physical role in vivo. This journal is

Synthesis of enantiopure structured triacylglycerols

The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.

PHOSPHATIDYLINOSITOL

The invention relates to a new pharmaceutical compound, diacyl phosphatdylinositol in which both the sn-1 and the sn-2 place are taken by stearic acid (18:0) (diacyl [18:0; 18:0] phosphatidylinositol), more preferably, wherein said diacyl phosphatidylinositol is compound 1 as depicted in Fig. 10 or a racemate of compounds 1 and 2 as depicted in Fig. 10. Said pharmaceutical compound and pharmaceutical compositions comprising this compound are specifically useful for the treatment of a disease or a condition wherein suppression of T-cell activation is desirable, such as asthma, diabetes Type 1, rheumatoid arthritis, inflammatory bowel disease or psoriasis. Also part of the invention are food items containing the compound(s) of the invention and use thereof in a diet to treat or prevent the disease or condition mentioned above

Synthesis of boron cluster lipids: Closo-dodecaborate as an alternative hydrophilic function of boronated liposomes for neutron capture therapy

(Chemical Equation Presented) We succeeded in the synthesis of the double-tailed boron cluster lipids 4a-c and 5a-c, which have a B 12H11S moiety as a hydrophilic function, by S-alkylation of B12H11SH (BSH) with bromoacetyl and chloroacetocarbamate derivatives of diacylglycerols for a liposomal boron delivery system on neutron capture therapy. Calcein encapsulation experiments revealed that the liposomes, prepared from the boron cluster lipid 4b, DMPC, PEG-DSPE, and cholesterol, are stable at 37°C in FBS solution for 24 h.

A simple and efficient method for direct acylation of acetals with long alkyl-chain carboxylic acid anhydrides

We have developed an efficient and simple method for direct transformation of acetals to carboxylic acid esters. The method consists of treatment of acetals with carboxylic anhydrides in the presence of boron trifluoride etherate as a catalyst and affords the corresponding ester derivatives in high yields with retention of configuration in the alcohol moiety. Some mechanistic aspects of this synthetically useful transformation are also discussed. (C) 2000 Elsevier Science Ltd.

Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses

Chiral sulfoquinovosyldiacylglycerols (SQDGs) have been synthesized to determine the absolute stereochemistry and the biological activities. The 1 H NMR spectrum of a natural SQDG is comparable to that of synthetic (2S)-SQDG rather than that of the (2R) analogue. The biological activity of the respective isomers for DNA polymerase α and β inhibition was not distinguishable in the enzymatic assay.