Diacetylenic phospholipids containing heteroatom near diacetylen

Details Diacetylenic phospholipids containing heteroatom near diacetylen Diacetylenic phospholipids containing heteroatom near diacetylen

1993-02-25

1994-03-01

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 80, 554 81, 556404, C07F 700, C07F 900

Patent

active

052909603

ABSTRACT:
Novel diacetylenic phospholipids having the diacetylenic moieties chemically decoupled from the rest of the acyl chains by the inclusion of one or more heteroatom, preferably oxygen, spacers on the acyl chains have the chemical formula: ##STR1## where m is 7, 8, 9, 10, 11, 12, or 13, where n is 8, 9, 10, 11, 12, or 13, where W is --O(CO)-- or --OCH.sub.2 --, where X is --CH.sub.2 --, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, or --SiMe.sub.2 CH.sub.2 --, where Y is --CH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 NH--, or --CH.sub.2 SiMe.sub.2 --, where Z is --N(CH.sub.3).sub.3, saccharide, or --ROH where R is --(CH.sub.2).sub.p -- and p is 0, 1, 2 or 3, and where X and Y are not both --CH.sub.2 --. Novel tubules made from these diacetylenic phospholipids have high flexibility and variable morphology.

REFERENCES:
patent: 4348329 (0000-01-01), Chapman
patent: 4867917 (1989-09-01), Singh et al.
Singh et al., "A General Method for the Synthesis of Diacetylenic Acids", inted in Synthetic Communications, 16(7)(1986), pp. 847-852.
Vaugh et al., J. Am. Chem. Soc'y 55, 3456 (1933).
Georger et al., "Helical and Tubular Microstructures Formed by Polymerizable Phosphatidylcholines", J. Am. Chem. Soc. 1987, 109, pp. 6169-6175.
Singh et al., "Self-Assembled Microstructures From a Polymerizable Ammonium Surfactant: Di(Hexacosa-12,14-Diynyl)Dimethylammonium Bromide", J. Chem. Soc. Chem. Commun., 1988, pp. 1222-1223.
Markowitz et al., "Self-Assembling Properties of 1,2-Diacyl-SN-Glycero-3-Phosphohydroxyethanol: A Headgroup-Modified Diacetylenic Phospholipid", Langmuir, vol. 7, No. 1, 1991, pp. 16-18.

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