Novel bisretinoids of human retina are lyso alkyl ether glycerophosphoethanolamine-bearing A2PE species was written by Kim, Hye Jin;Sparrow, Janet R.. And the article was included in Journal of Lipid Research in 2018.Formula: C37H74NO8P The following contents are mentioned in the article:
Bisretinoids are a family of fluorophores that form in photoreceptor cells′ outer segments by nonenzymic reaction of two vitamin A aldehydes (A2) with phosphatidylethanolamine (PE). Bisretinoid fluorophores are the major constituents of the lipofuscin of retinal pigment epithelium (RPE) that accumulate with age and contribute to some retinal diseases. Here, we report the identification of a previously unknown fluorescent bisretinoid. By ultra-performance LC (UPLC) coupled to photodiode array detection, fluorescence (FLR), and ESI-MS, we determined that this novel bisretinoid is 1-octadecyl-2-lyso-sn-glycero A2PE (alkyl ether lysoA2PE). This structural assignment was based on mol. mass (m/z 998), UV-visible absorbance maxima (340 and 440 nm), and retention time (73 min) and was corroborated by biomimetic synthesis using all-trans-retinal and glycerophosphoethanolamine analogs as starting materials. UPLC profiles of ocular extracts acquired from human donor eyes revealed that alkyl ether lysoA2PE was detectable in RPE, but not neural retina. LysoA2PE FLR spectra exhibited a significant hyperchromic shift in hydrophobic environments. The propensity for lysoA2PE to undergo photooxidation/degradation was less pronounced than A2E. In mechanistic studies, A2PE was hydrolyzed by phospholipase A2 and plasmalogen lysoA2PE was cleaved under acidic conditions. The characterization of these addnl. members of the bisretinoid family advances our understanding of the mechanisms underlying bisretinoid biogenesis. This study involved multiple reactions and reactants, such as (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dipalmitate (cas: 923-61-5Formula: C37H74NO8P).
(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dipalmitate (cas: 923-61-5) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Formula: C37H74NO8P
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts