Synthesis of N-heteroaryl retinals and their artificial bacteriorhodopsins

Susana López, Virginia Rodríguez, Javier Montenegro, Carlos Saá, Rosana Alvarez, Carlos Silva López, Angel R. De Lera, Rosana Simón, Tzvetana Lazarova, Esteve Padrós

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

N-Heteroaryl retinals derived from indole, 1-indolizine and 3-indolizine (10a-c) have been synthesized after their UV/Vis red-shifted absorption properties had been predicted by time-dependent density functional theory (TD-DFT) computations. The three new analogues form artificial pigments upon recombination with bacterioopsin: indolyl retinal 10a undergoes fast and efficient reconstitution to form a species with a UV/Vis absorbance maximum similar to that of wild-type bacteriorhodopsin, whilst the indolizinyl retinals 10b and 10c also reconstitute in significant proportion to give noticeably red-shifted, although unstable, pigments. Significant changes in the pK a values of these artificial bacteriorhodopsins are interpreted as arising from nonoptimal binding-site occupancy by the chromophore due to steric constraints. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
Original languageEnglish
Pages (from-to)2078-2087
JournalChemBioChem
Volume6
DOIs
Publication statusPublished - 1 Nov 2005

Keywords

  • Ab initio calculations
  • Artificial bacteriorhodopsins
  • Dyes/pigments
  • N-heteroaryl retinals
  • UV-visible spectra simulation

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