Synthese und Aggregationsverhalten chiraler Cystein‐Amphiphile mit s‐Triazin als verknüpfende Partialstruktur

Abstract

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.

Acetylene-bridged triazine-conjugated structures: synthesis and liquidcrystalline properties

“…The material obtained was purified by column chromatography with hexane/ethyl acetate (19:1) as an eluent to give white solid materials (3.5 g, yield: 70%) 1 H NMR (500 MHz, CDCl 3 ) δ 3.70 (t, J = 6.7 Hz, 4H, OCH 2 ) , 1.81-1.51 (m, 4H, CH 2 ) , 1.58-1.20 (m, 36H, CH 2 ), 0.94 (t, J = 6.9 Hz, 6H CH 3 ) . 13 C NMR (126 MHz, CDCl 3 ) δ 173.2, 172.2, 68.5, 32.0, 29.7 (2C), 29.6 (2C), 29.4, 29.3, 28.7, 25.9, 22.7, 14.1.…”

“…1 H NMR (500 MHz, CDCl 3 ) δ 3.92 (s, 1H), 3.52 (t, J = 6.7 Hz, 4H, OCH 2 ), 1.50-1.40 (m, 4H, CH 2 ) , 1.33-1.08 (m, 36H, CH 2 ) , 0.77 (t, J = 6.8 Hz, 6H, CH 3 ) . 13 n-BuLi (0.65 mL, 1.05 mmol, 1.6 M in hexane) was added dropwise to a stirred solution of 2,4-bis(dodecyloxy)-6ethynyl-1,3,5-triazine (2) (0.5 g, 1.05 mmol) in THF (8 mL) at -78 • C The solution was stirred for 1 h, allowed to warm to room temperature, and stirred for another 20 min. The solution was then cooled to -78 • C and a solution of cyanuric chloride (1) (0.055 mg, 0.3 mmol) in THF (1 mL) was added dropwise and the mixture was stirred for 30 min.…”

“…1 H NMR (500 MHz, CDCl 3 ) δ 3.63 (t, J = 6.7 Hz, 12H, OCH 2 ), 1.64-1.50 (m, 12H, CH 2 ) , 1.44-1.22 (m, 108H, CH 2 ) , 0.88 (t, J = 7.0 Hz, 18H, CH 3 ) 13. C NMR (126 MHz, CDCl 3 ) δ 173.4, 173.0, 172.4, 92.8, 90.4, 68.8, 32.2, 30.0, 29.9 (2C), 29.8, 29.6 (2C), 28.9, 26.1, 23.0, 14.4).…”

Triazinyl-Amino Acids, New Building Blocks for Pseudopeptides

“…10 For synthetic ease, however, our initial designs utilize ethylenediamine (EDA) and glycine as in molecule 1. Triazines conjugated to amino acids have been employed in other contexts, particularly in materials chemistry 11 and as dyes or inks, 12 and they have received some attention as combinatorial scaffolds, 13 but we believe that this particular orientation of functional groups has not yet been exploited in construction of oligomers. Figure 1 shows that these kinds of triazinyl amino acids are equivalent in length to about three and one-half amino acids.…”

Use of a Boroxazolidone Complex of 3-Iodo-l-tyrosine for Palladium-Catalyzed Cross-Coupling

“…At first, the B,B -diphenyl boroxazolidone of 3-iodo- l -tyrosine was considered since this derivative was expected to be more stable than a corresponding alkyl derivative and a number of such complexes of amino acids had already been described in the literature. ,,− For synthetic ease, the air-stable reagent NaBPh 4 was selected over Ph 3 B to generate the boroxazolidone. Although the desired product was obtained in high yield (94%), an 18 h reflux in aq HCl was required (Supporting Information).…”