Literature DB >> 8391868

pKa of the protonated Schiff base of bovine rhodopsin. A study with artificial pigments.

G Steinberg1, M Ottolenghi, M Sheves.   

Abstract

Artificial bovine rhodopsin pigments derived from synthetic retinal analogues carrying electron-withdrawing substituents (fluorine and chlorine) were prepared. The effects of the electron withdrawing substituents on the pKa values of the pigments and on the corresponding Schiff bases in solution were analyzed. The data suggest that the apparent pKa of the protonated Schiff base is above 16. However, the alternative possibility that the retinal Schiff base linkage in bovine rhodopsin is not accessible for titration from the aqueous bulk medium cannot be definitely ruled out.

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Year:  1993        PMID： 8391868      PMCID： PMC1262475          DOI： 10.1016/S0006-3495(93)81518-2

Source DB:  PubMed          Journal:  Biophys J        ISSN： 0006-3495            Impact factor:   4.033


  14 in total

1.  High-pH form of bovine rhodopsin.

Authors:  Y Koutalos
Journal:  Biophys J       Date:  1992-01       Impact factor: 4.033

2.  NMR studies of fluorinated visual pigment analogs.

Authors:  L U Colmenares; A E Asato; M Denny; D Mead; J P Zingoni; R S Liu
Journal:  Biochem Biophys Res Commun       Date:  1991-09-30       Impact factor: 3.575

Review 3.  Nature of the primary photochemical events in rhodopsin and bacteriorhodopsin.

Authors:  R R Birge
Journal:  Biochim Biophys Acta       Date:  1990-04-26

4.  Deprotonation of the Schiff base of rhodopsin is obligate in the activation of the G protein.

Authors:  C Longstaff; R D Calhoon; R R Rando
Journal:  Proc Natl Acad Sci U S A       Date:  1986-06       Impact factor: 11.205

5.  Effect of carboxylic acid side chains on the absorption maximum of visual pigments.

Authors:  E A Zhukovsky; D D Oprian
Journal:  Science       Date:  1989-11-17       Impact factor: 47.728

6.  Removal of the 9-methyl group of retinal inhibits signal transduction in the visual process. A Fourier transform infrared and biochemical investigation.

Authors:  U M Ganter; E D Schmid; D Perez-Sala; R R Rando; F Siebert
Journal:  Biochemistry       Date:  1989-07-11       Impact factor: 3.162

7.  Photolysis intermediates of the artificial visual pigment cis-5,6-dihydro-isorhodopsin.

Authors:  A Albeck; N Friedman; M Ottolenghi; M Sheves; C M Einterz; S J Hug; J W Lewis; D S Kliger
Journal:  Biophys J       Date:  1989-02       Impact factor: 4.033

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

Authors:  M Sheves; A Albeck; N Friedman; M Ottolenghi
Journal:  Proc Natl Acad Sci U S A       Date:  1986-05       Impact factor: 11.205

Review 9.  Photophysics of light transduction in rhodopsin and bacteriorhodopsin.

Authors:  R R Birge
Journal:  Annu Rev Biophys Bioeng       Date:  1981

10.  Determinants of visual pigment absorbance: identification of the retinylidene Schiff's base counterion in bovine rhodopsin.

Authors:  J Nathans
Journal:  Biochemistry       Date:  1990-10-16       Impact factor: 3.162
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  17 in total

1.  Molecular mechanism of spontaneous pigment activation in retinal cones.

Authors:  Alapakkam P Sampath; Denis A Baylor
Journal:  Biophys J       Date:  2002-07       Impact factor: 4.033

2.  The unusual pK(a) of the rhodopsin chromophore: Is this how nature minimizes photoreceptor noise?

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

Review 3.  Microbial and animal rhodopsins: structures, functions, and molecular mechanisms.

Authors:  Oliver P Ernst; David T Lodowski; Marcus Elstner; Peter Hegemann; Leonid S Brown; Hideki Kandori
Journal:  Chem Rev       Date:  2013-12-23       Impact factor: 60.622

4.  Magic angle spinning NMR of the protonated retinylidene Schiff base nitrogen in rhodopsin: expression of 15N-lysine- and 13C-glycine-labeled opsin in a stable cell line.

Authors:  M Eilers; P J Reeves; W Ying; H G Khorana; S O Smith
Journal:  Proc Natl Acad Sci U S A       Date:  1999-01-19       Impact factor: 11.205

5.  Function of extracellular loop 2 in rhodopsin: glutamic acid 181 modulates stability and absorption wavelength of metarhodopsin II.

Authors:  Elsa C Y Yan; Manija A Kazmi; Soma De; Belinda S W Chang; Christoph Seibert; Ethan P Marin; Richard A Mathies; Thomas P Sakmar
Journal:  Biochemistry       Date:  2002-03-19       Impact factor: 3.162

6.  Rational design of a colorimetric pH sensor from a soluble retinoic acid chaperone.

Authors:  Tetyana Berbasova; Meisam Nosrati; Chrysoula Vasileiou; Wenjing Wang; Kin Sing Stephen Lee; Ipek Yapici; James H Geiger; Babak Borhan
Journal:  J Am Chem Soc       Date:  2013-10-18       Impact factor: 15.419

7.  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

8.  The role of the non-covalent β-ionone-ring binding site in rhodopsin: historical and physiological perspective.

Authors:  Hiroyuki Matsumoto; Tatsuo Iwasa; Tôru Yoshizawa
Journal:  Photochem Photobiol Sci       Date:  2015-11       Impact factor: 3.982

9.  Vertebrate ultraviolet visual pigments: protonation of the retinylidene Schiff base and a counterion switch during photoactivation.

Authors:  Ana Karin Kusnetzow; Abhiram Dukkipati; Kunnel R Babu; Lavoisier Ramos; Barry E Knox; Robert R Birge
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-19       Impact factor: 11.205

10.  Helix movement is coupled to displacement of the second extracellular loop in rhodopsin activation.

Authors:  Shivani Ahuja; Viktor Hornak; Elsa C Y Yan; Natalie Syrett; Joseph A Goncalves; Amiram Hirshfeld; Martine Ziliox; Thomas P Sakmar; Mordechai Sheves; Philip J Reeves; Steven O Smith; Markus Eilers
Journal:  Nat Struct Mol Biol       Date:  2009-02-01       Impact factor: 15.369
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