Synthesis of First Phospholipids from 2,2,6,6‐Tetrakis(hydroxymethyl)cyclohexanol.

Abstract

Lipids U 0750Synthesis of First Phospholipids from 2,2,6,6-Tetrakis(hydroxymethyl)cyclohexanol. -New phospholipid systems containing a carbocyclic polyol fragment are synthesized. Compound (VIII) is synthesized as a model of terminal choline thio phospholipid. Apart from phosphocholine derivative (VIII), thiophosphate (VI) is used to prepare the model diol phospholipid (X). Reaction of acetal (III) with further phosphorus-containing heterocyclic compounds afford cationic ammonium amidophosphorus lipid models (e.g. cholesterol phospholipid). -(PREDVODITELEV, D. A.; SAVIN, G. A.; MALENKOVSKAYA, M. A.; NIFANT'EV, E. E.; Russ.

Cationic Nitrophospoamphiphiles of Phosphonate and Amidophosphonate Types

“…Among the cationic lipids included into these liposomes are widely studied ammonium phosphorus-free lipids [8][9][10][11][12]. At the same time the positively charged ammonium (cationic) phospholipids are far less understood [8,[13][14][15][16], although the pioneering study of cationic phospholipides preparation by an example of glycerophosphonate analogs has been performed more than 25 years ago [17].The present report concerns syntheses of new cationic lipid phosphonoamphiphiles proceeding from the acetone derivative of tris(hydroxymethyl)nitromethane (I). The choice of the trimethylolnitromethane core for the new lipid systems aimed at application in the genetic therapy was determined by the synthetic availability of the initial compound, its polarity, and also by the photosensitivity of its phospholipide derivatives.…”

“…Among the cationic lipids included into these liposomes are widely studied ammonium phosphorus-free lipids [8][9][10][11][12]. At the same time the positively charged ammonium (cationic) phospholipids are far less understood [8,[13][14][15][16], although the pioneering study of cationic phospholipides preparation by an example of glycerophosphonate analogs has been performed more than 25 years ago [17].…”