Faculty Works

Title

Retinylidene Schiff bases in phosphatidylcholine reverse micelles: formation, protonation and stability

Document Type

Article

Publication Date

1991

Abstract

All-trans-N-retinylidene-n-butylamine 3 has been formed in inverted micelles of phosphatidylcholine (PC)–hexane containing varying amounts of water ([H2O]/[PC]= 0–3) and the formation, protonation and stability have been studied. The micelles have been found to catalyse the Schiff-base formation. The Schiff-base was found to be stable in the presence of structured water molecules bonded to the polar head groups of the micelles. A larger water-pool causes the decomposition of the Schiff-base. Schiff-base 3 intercalated in the inverted micelle was found to undergo protonation in the presence of 3-chloropropionic acid, the extent of which depended on the water-pool size. The results are discussed in terms of the formation, protonation and stability of retinylidene Schiff-base chromophores in rhodopsins.

Publication Title

Journal of the Chemical Society, Perkin Transactions 2

Start Page No.

1785

End Page No.

1789

ISSN

1364-5471

DOI

10.1039/P29910001785

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