Retinylidene schiff bases in alkylammonium carboxylate reversed micelles

Singh, Anil K. ; Sandorfy, Camille ; Fendler, Janos H. (1990) Retinylidene schiff bases in alkylammonium carboxylate reversed micelles Biochimica et Biophysica Acta (BBA) - General Subjects, 1036 (1). pp. 34-40. ISSN 0304-4165

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All-trans-retinal, incorporated into dodecylammonium propionate, dodecylammonium 3-chloropropionate and dodecylammonium trifluoroacetate reversed micelles in cyclohexane containing different amounts of solubilized water, gave all-trans-N-retinylidene-n-dodecylamine. Formation of all-trans-N-retinylidene-n-dodecylamine was complete within a few minutes when all-trans-retinal was solubilized along with L-lysine in reversed-micellar dodecylammonium propionate in cyclohexane as compared to the several hours required for the comparable reaction to occur in the absence of lysine. In situ formed all-trans-N-retinylidene-n-dodecylamine was not protonated by the acidic moiety (i.e., propionate, 3-chloropropionate or trifluoroacetate anions) of dodecylammonium propionate, dodecylammonium 3-chloropropionate or dodecylammonium trifluoroacetate reversed micelles. Addition of propionic or 3-chloropropionic acid did not cause observable protonation of the reversed-micelle-incorporated all-trans-N-retinylidene-n-dedecylamine. Addition of strong trifluoroacetic acid to reversed micellar solutions of all-trans-N-retinylidene-n-dodecylamine caused protonation as well as hydrolysis to retinal. Retinylidene Schiff bases are protected from protonation by strongly held surfactant-ion pairs which may model proton channels whose function is controlled by protein conformational changes.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Retinylidene; Schiff Base Chromophore; Reversed Micelle; Micelle; Reversed; Rhodopsin; Alkylammonium Carboxylate Surfactant
ID Code:54094
Deposited On:11 Aug 2011 11:44
Last Modified:11 Aug 2011 11:44

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