Es werden homologe Liposomenbausteine 3 mit L‐Cystein als chirale hydrophile Kopfgruppe synthetisiert. Als Verknüpfungseinheit zwischen Cystein und den lipophilen Alkylketten dient s‐Triazin. Mittels DSC‐ und Fluoreszenz‐Anisotropie‐Messungen lassen sich die Phasenübergangstemperaturen der Lipide bestimmen. Es kann gezeigt werden, daß eine den Phospholipiden analoge Relation zwischen Art und Länge der Ketten und der Phasenübergangstemperatur besteht. Einschlußversuche mit ionischen wasserlöslichen Farbstoffen ergeben Hinweise auf eine Interaktion der in Phosphatpuffer (pH = 7.0), gebildeten Vesikel mit kationischen, nicht jedoch mit anionischen hydrophilen Substanzen.

ChemInform Abstract Various homologous liposome building blocks of type (IV) with L-cysteine as chiral hydrophilic head group are synthesized starting from the known chelate (I) via the preamphiphiles (III). s-Triazine serves as connecting unit between cysteine and the lipophilic alkyl chains. The phase transition temp. of the lipids are determined by DSC or fluorescence anisotropy. It can be shown that the relationship between nature and length of the chains and the phase transition temp. corresponds to that of phospholipids. Encapsulation experiments with ionic water-soluble dyes give some hints that the vesicles prepared in phosphate buffer (pH 7.0) interact with cationic but not with anionic hydrophilic substances.

ChemInform Abstract A number of s-triazine derivatives are prepared with a view to developing a variable system of chiral amphiphiles for the study of the effect of chirality on the formation and properties of liposomes. These target amphiphiles, represented in the scheme by (III) and (VI), possess either one or two lipophilic chains and L-cysteine, L-serine or L-lysine as the hydrophilic moiety (permitting TLC determination of the optical purity). Only the cysteine derivatives with two alkyl chains, i.e. (VI), can be induced to form vesicles on sonication.

Pantolactone (I) is used to build up a new class of chiral analogues of diacylglyceroles, e.g. the pentamide esters (VI).