Hydroxycholesterol-25 interacts differently with lipids of the inner and outer membrane leaflet-The Langmuir monolayer study complemented with theoretical calculations was written by Wnetrzak, Anita;Chachaj-Brekiesz, Anna;Kus, Karolina;Filiczkowska, Anna;Lipiec, Ewelina;Kobierski, Jan;Petelska, Aneta D.;Dynarowicz-Latka, Patrycja. And the article was included in Journal of Steroid Biochemistry and Molecular Biology in 2021.Synthetic Route of C39H76NO8P The following contents are mentioned in the article:
25-Hydroxycholesterol (25-OH), a mol. with unusual behavior at the air/water interface, being anchored to the water surface alternatively with a hydroxyl group at C(3) or C(25), has been investigated in mixtures with main membrane phospholipids (phosphatidylcholines – PCs, and phosphatidylethanolamines – PEs), characteristic of the outer and inner membrane leaflet, resp. To achieve this goal, the classical Langmuir monolayer approach based on thermodn. anal. of interactions was conducted in addition to microscopic imaging of films (in situ with BAM and after transfer onto mica with AFM), surface-sensitive spectroscopy (PM-IRRAS), as well as theor. calculations Our results show that the strength of interactions is primarily determined by the kind of polar group (strong, attractive interactions leading to surface complexes formation were found to occur with PCs while weak or repulsive ones with PEs). Subsequently, the saturation of phosphatidylcholines apolar chain(s) was found to be crucial for the structure of the formed complexes. Namely, saturated PC (DPPC) does not have preferences regarding the orientation of 25-OH mol. in surface complexes (which results in the two possible 25-OH arrangements), while unsaturated PC (DOPC) enforces one specific orientation of oxysterol (with C(3)-OH group). Our findings suggest that the transport of 25-OH between inner and outer membrane leaflet can proceed without orientation changes, which is thermodynamically advantageous. This explains results found in real systems showing significant differences in the rate of transmembrane transport of 25-OH and the other chain-oxidized oxysterols compared to their ring-oxidized analogs or cholesterol. This study involved multiple reactions and reactants, such as (2R,9Z)-1-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-3-(palmitoyloxy)propan-2-yl oleate (cas: 26662-94-2Synthetic Route of C39H76NO8P).
(2R,9Z)-1-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-3-(palmitoyloxy)propan-2-yl oleate (cas: 26662-94-2) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esters contain a carbonyl center, which gives rise to 120掳 C鈥揅鈥揙 and O鈥揅鈥揙 angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C鈥揙鈥揅 bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Synthetic Route of C39H76NO8P
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics