Properties of unusual phospholipids: I. Synthesis, monolayer investigations and calorimetry of diacylglycerophosphocholines containing monoacetylenic acyl chains.
Isomeric diacylglycerophosphocholines containing various octadecynoic acids (4-, 6-, 9-, 12-, 14- and 17-octadecynoic acid) were synthesized and purified to homogeneity. Their behaviour in monolayers, when studied by the Langmuir-Blodgett film balance technique, revealed systematic relationships between structure and packing properties. The thermotropic phase behaviour of these novel phospholipids, as measured by differential scanning calorimetry, depended in a systematic fashion on the position of the triple bond: the gel-to-liquid-crystalline phase transition temperature (Tm) passed through a minimum of -3.4 degrees C for a triple bond in position 9.
Rürup
J
J
Bereich Enzymtechnologie/Naturstoffchemie der GBF, Gesellschaft für Biotechnologische Forschung mbH, Braunschweig, Germany.
Mannova
M
M
Brezesinski
G
G
Schmid
R D
RD
D002152:Calorimetry, Differential Scanning; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D007536:Isomerism; D010713:Phosphatidylcholines / Q000138:chemical synthesis* / Q000737:chemistry*; D010743:Phospholipids / Q000096:biosynthesis* / Q000138:chemical synthesis / Q000737:chemistry*
D005231:Fatty Acids, Unsaturated; D010713:Phosphatidylcholines; D010743:Phospholipids