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Literature DB >> 3458179

Controlling the pKa of the bacteriorhodopsin Schiff base by use of artificial retinal analogues.

M Sheves, A Albeck, N Friedman, M Ottolenghi.

Abstract

Artificial bacteriorhodopsin pigments based on synthetic retinal analogues carrying an electron-withdrawing CF3 substituent group were prepared. The effects of CF3 on the spectra, photocycles, and Schiff base pKa values of the pigments were analyzed. A reduction of 5 units in the pKa of the Schiff base is observed when the CF3 substituent is located at the C-13 polyene position, in the vicinity of the protonated Schiff base nitrogen. The results lead to the unambiguous characterization of the (direct) titration of the Schiff base in bacteriorhodopsin and to the conclusion that the deprotonation rate of the Schiff base during the photocycle (i.e., the generation of the M412 intermediate) is determined by a structural change in the protein.

Entities: Chemical

Mesh：

Substances：

Year: 1986 PMID： 3458179 PMCID： PMC323493 DOI： 10.1073/pnas.83.10.3262

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

19 in total

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Journal: Biochemistry Date: 1975-06-03 Impact factor: 3.162

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Journal: Biochim Biophys Acta Date: 1979-03-14

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Journal: FEBS Lett Date: 1979-04-15 Impact factor: 4.124

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Journal: J Biol Chem Date: 1978-09-10 Impact factor: 5.157

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Journal: FEBS Lett Date: 1978-09-15 Impact factor: 4.124

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Journal: Annu Rev Biophys Bioeng Date: 1981

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Journal: Biochemistry Date: 1981-02-03 Impact factor: 3.162

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Authors: T Schreckenbach; B Walckhoff; D Oesterhelt
Journal: Biochemistry Date: 1978-12-12 Impact factor: 3.162

30 in total

1. Molecular dynamics study of the nature and origin of retinal's twisted structure in bacteriorhodopsin.

Authors: E Tajkhorshid; J Baudry; K Schulten; S Suhai
Journal: Biophys J Date: 2000-02 Impact factor: 4.033

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Authors: S Geibel; T Friedrich; P Ormos; P G Wood; G Nagel; E Bamberg
Journal: Biophys J Date: 2001-10 Impact factor: 4.033

3. Octopus photoreceptor membranes. Surface charge density and pK of the Schiff base of the pigments.

Authors: Y Koutalos; T G Ebrey; H R Gilson; B Honig
Journal: Biophys J Date: 1990-08 Impact factor: 4.033

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Authors: R R Birge
Journal: Biophys J Date: 1993-05 Impact factor: 4.033

5. Protonation state of Asp (Glu)-85 regulates the purple-to-blue transition in bacteriorhodopsin mutants Arg-82----Ala and Asp-85----Glu: the blue form is inactive in proton translocation.

Authors: S Subramaniam; T Marti; H G Khorana
Journal: Proc Natl Acad Sci U S A Date: 1990-02 Impact factor: 11.205

6. Substitution of amino acids Asp-85, Asp-212, and Arg-82 in bacteriorhodopsin affects the proton release phase of the pump and the pK of the Schiff base.

Authors: H Otto; T Marti; M Holz; T Mogi; L J Stern; F Engel; H G Khorana; M P Heyn
Journal: Proc Natl Acad Sci U S A Date: 1990-02 Impact factor: 11.205

7. Voltage dependence of proton pumping by bacteriorhodopsin is regulated by the voltage-sensitive ratio of M1 to M2.

Authors: G Nagel; B Kelety; B Möckel; G Büldt; E Bamberg
Journal: Biophys J Date: 1998-01 Impact factor: 4.033

8. Evidence for a controlling role of water in producing the native bacteriorhodopsin structure.

Authors: I Rousso; N Friedman; A Lewis; M Sheves
Journal: Biophys J Date: 1997-10 Impact factor: 4.033

9. Evidence for a bound water molecule next to the retinal Schiff base in bacteriorhodopsin and rhodopsin: a resonance Raman study of the Schiff base hydrogen/deuterium exchange.

Authors: H Deng; L Huang; R Callender; T Ebrey
Journal: Biophys J Date: 1994-04 Impact factor: 4.033

10. Elucidating the exact role of engineered CRABPII residues for the formation of a retinal protonated Schiff base.

Authors: Chrysoula Vasileiou; Wenjing Wang; Xiaofei Jia; Kin Sing Stephen Lee; Camille T Watson; James H Geiger; Babak Borhan
Journal: Proteins Date: 2009-12