Tetraether lipids with small headgroups, method of their synthesis and uses thereof

摘要

Tetraether lipid compounds with small head groups are new. Tetraether lipid compounds (I) with small head groups of formula (1) are new. R, R1 = CH2I, CH2IO3, CH2Br, CH2ONa, (CH2NX3)+, CH2-pyridinum derivatives, CH2-tosylate, CH2SCN, CH2NCO, CH2NNH, CH2=ethylene oxirane, CH2N3, a silane of formula (A)-Si(B)b(D)c (2), a halogenated alkanyl, alkenyl, alkanylether or alkenylether, preferably CH2CF3, CH2CF2CF3, CH2OCF2CF3, derivatized alkanyls and alkanylethers of formula (3)-(5), CH2-(A)a-(B) (3), -CH2-O-(A)a-(B) (4), CH2-NH-(A)a-(B) (5); X = alkane or aromatic; A = -CH2, -CH2O-, -CH2O(CH2)x, -CH2O(CH2)x-O-, -CH2-(CH2)x-O-; x = 1-30; B = Cl, Br, I, F, OH; D = -OCH3, -OCH2CH3, -CH3, -Ophenyl, -Obenzyl, -OCF3, -OCF2CF3, -CF3, glucose, mannose, galactose or other glycosides; A1 = CH2, CH2O-, CH2CH2O-, CF2, CF2O, CF2CF2O; B1 = OH, NH2, SH, COOH, COCl, CONH2, CH3, CH=CH2, -CCH, SCN, CN, N=NH, N3 or -N(X1)3; and X1 = CH3, OCH3, OCH2CH3 or pyridine, phenol, benzene, mono, di or polysaccharides, biotin, peptides, proteins, antibodies, avidins, lectins or oligonucleotides. An Independent claim is included for a process for the preparation of tetraether lipids (I) from a bacterial lipid extract, isolated by biotechnological means, by full cleavage of all natural head groups by reaction with pyridine hydrochloride or hydrolysis with hydrogen halides with subsequent purification.