Synthesis of six novel retinals and their interaction with bacterioopsin

✍ Scribed by M. Groesbeek; Y. G. Kirillova; R. Boeff; J. Lugtenburg

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 943 KB
• Volume: 113
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19941130107

✦ Synopsis

Abstract

The synthesis and spectroscopic characterization of six novel chemically modified retinals, is described, prepared by a single strategy: all‐E‐10,12‐ethanoretinal (1), all‐E‐10,12‐propanoretinal (2), all‐E‐10,12‐ethano‐20‐norretinal (3), all‐E‐20‐nor‐10,12‐propanoretinal (4), all‐E‐12,14‐ethano‐20‐norretinal (5), and all‐E‐20‐nor‐12,14‐propanoretinal (6). For this strategy we developed two novel synthons, 2‐(diethoxyphosphinyl) hexanedinitrile and 2‐(diethoxyphosphinyl) heptanedinitrile which were prepared in their deprotonated form from hexanedinitrile and heptanedinitrile. Bacterioopsin was incubated with each of 1 to 6. Only 1 and 3 form bacteriorhodopsin analogues (bR‐1 and bR‐3). bR‐1 shows light‐dark adaptation and an approx. 50% light‐driven proton‐pump action. bR‐3 does not show light‐dark adaptation or proton‐pump action. It is also shown that the protein can efficiently accommodate retinal with the 10,12‐ethano group whereas the corresponding retinal with the 10,12‐propano group does not fit in the binding site.