Summary
Azobenzene amphiphiles containingβ-alanine, L-lysine orβ-homolysine moieties were synthesized and characterised. Stable monomolecular layers at the air/water interface and LB multilayers has been obtained from some of them. One sample of azobenzenes synthesized has been shown to undergo a reversible trans/cis photoisomerization upon light irradiation in both solution and LB multilayer.
Similar content being viewed by others
Abbreviations
- DCC:
-
N,N′-dicyclohexyl carbodiimide
- HONSu:
-
N-hydroxy succinimide
- Boc:
-
t-butyloxycarbonyl
- But :
-
t-butyl
- EtOAc:
-
ethyl acetate
- THF:
-
tetrahydrofuran
- TEA:
-
triethylamine
- HPLC:
-
high performance liquid chromatography
- TLC:
-
thin layer chromatography
- Ph:
-
phenyl
- i-PrOH:
-
isopropyl alcohol
References
Anzai J-i, Lee S, Osa T (1989) Reactive Langmuir-Blodgett membrane for biosensor applications. Use of succinimidyl behenoate-based membranes as support for covalently immobilizingα-chymotrypsin. Bull Chem Soc Japan 62: 3018–3020
Denny JB, Blobel G (1984)125J-labeled crosslinking reagent that is hydrophilic photoactivatable and cleavable through an azo linkage. Proc Natl Acad Sci USA 81: 5286–5290
Freimanis J, Markava E, Matisova G, Gerca L, Muzikante I, Rutkis M, Silinsh E (1994) (Methylacylamino)azobenzene derivatives for photoresponsive monomolecular layers. Langmuir 10: 3311–3314
Landau EM, Grayer Wolf S, Sagiv J, Deutsch M, Kjaer K, Als-Nielsen J, Leiserowitz L, Lahav M (1989) Design and surface synchrotron X-ray structure analysis of Langmuir films for crystal nucleation. Pure Appl Chem. 61: 673–684
Liu ZF, Loo BH, Baba R, Fujishima A (1990) Excellent reversible photochromic behaviour of 4-octyl-4′-(5-carboxylpentamethyleneoxy)-azobenzene in organized monolayer assemblies. Chem Lett 1023–1026
Markava E, Freimanis J, Gailite V, Kaula I, Matisova G, Rutkis M, Aleksandrov SB, Ilchenko AYa, Kolotilo NV (1992) New amphiphilic diacetyleneβ-aminoacid for polar LB films. Latvian J Chem 604–607
Markava E, Freimanis J, Gailite V, Kaula I, Matisova G, Rutkis M, Aleksandrov SB, Gerca L (1993) Some new surfactants based on amino acids. Latvian J Chem 453–459
Menzel H, Hallensleben ML, Schmidt A, Knoll W, Fischer T, Stumpe J (1993) LB films of photochromic polyglutamates. 4. Spectroscopic and structural studies on LB films of copolyglutamates bearing azobenzene moieties and long alkyl chains. Macromol 26: 3644–3649
Murphy HR, Harris HW Jr (1987) Improved synthesis and iodination of a cleavable photoactive probe. Anal Biochem 165: 88–95
Popowitz-Biro R, Hill K, Shavit E, Hung DJ, Lahav M, Leiserowitz L, Sagiv J, Hsiung H, Meredith GR, Vanherzeele H (1990) A new series of amphiphilic molecules forming stable Z-type (polar) Langmuir-Blodgett films. J Am Chem Soc 112: 2498–2506
Sato T, Okazaki Y, Iriyama K (1994) Molecular aggregation and photoisomerization of LB films of azobenzene-containing long-chain fatty acids and their salts studied by UV-VIS and infrared spectroscopy. Langmuir 10: 2363–2369
Seki T, Sakuragi M, Kawanishi Y, Suzuki Y, Tamaki T, Fukuda R, Ichimura K (1993) “Command surfaces” of LB films. Photoregulation of LC alignement by molecularly tailored surface azobenzene layers. Langmuir 9: 211–218
Xu X, Era M, Tsutsui T, Saito S (1989) Control of aggregated structures in monolayers and multilayers by mixing at the molecular level of two azobenzene-linked amphiphiles. Thin Solid Films 178: 541–547
Yamamoto H, Nishida A (1988) Photoresponsive peptide and polypeptide systems. VI Reversible solubility change of azo aromatic lysine. Bull Chem Soc Japan 61: 2201–2202
Yamamoto H, Nishida A, Takimoto T, Nagai A (1990) Photoresponsive peptide and polypeptide systems. VIII Synthesis and reversible photochromism of azoaromatic poly-(L-ornithine). J Polym Sci A 28: 67–74
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Markava, E., Matisova, G., Gerca, L. et al. Photoactive amino acid derivatives with long alkyl chains. Amino Acids 10, 333–343 (1996). https://doi.org/10.1007/BF00805861
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00805861