FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2053185148> ?p ?o ?g. }

• W2053185148 endingPage "2988" @default.
• W2053185148 startingPage "2976" @default.
• W2053185148 abstract "In order to generate potential chemical cross-links for studying the chromophore binding site of bacteriorhodopsin and related helix-bundle proteins, MnO2 was used to oxidize all-trans-retinal's ring moiety. The structures and solution conformations of three ring-oxidized retinal analogues have been determined by using UV-visible absorption and 1H and 13C NMR spectroscopies, primarily with regard to (i) the introduction of a functional group at the ring end of the chromophore, (ii) the retention of the all-trans geometry of the polyenal side chain, and (iii) the torsional angle of the ring-polyenal bond. Analyses of their UV-visible absorption spectral parameters (lambda max, epsilon max, and vibrational fine structure) and NMR spectral parameters (1H-1H coupling constants, 1H and 13C NMR chemical shifts, and 1H homonuclear Overhauser effects) indicated the 4-oxo and the 2,3-dehydro-4-oxo derivatives both possess the twisted 6-s-cis conformation adopted by most six-membered ring analogues of retinal in solution or crystal. However, the alpha-dioxocyclopentenyl analogue exists in solution predominantly (70-80%) as the planar 6-s-trans conformer, similar to violerythrine chromophore analogues. In order to identify the minor solution forms, molecular modeling and geometry optimizations using the semiempirical molecular orbital method AM1 defined two additional symmetry-related minima at +/- 30-40 degrees in its C6-C7 torsional energy profile. Because the chromophores of bacterio- and halorhodopsins and sensory rhodopsins are bound as the 6-s-trans conformer [Harbison, G.S., Smith, S.O., Pardoen, J.A., Courtin, J.M.L., Lugtenburg, J., Herzfeld, J., Mathies, R.A., & Griffin, R.G. (1985) Biochemistry 24, 6955-6962; Baselt, D.R., Fodor, S.P.A., van der Steen, R., Lugtenburg, J., Bogomolni, R.A., & Mathies, R.A. (1989) Biophys. J. 55, 193-196], we suggest that the cyclopentenyl analogue's alpha-diketo function may be favorably positioned within the binding pocket and sufficiently reactive toward nucleophilic attack to cross-link an arginine located in or near the ring end of the chromophore cavity: Arg134 according to the current model of bacteriorhodopsin's tertiary structure [Henderson, R., Baldwin, J.M., Ceska, T.A., Zemlin, F., Beckmann, E., & Downing, K.H. (1990) J. Mol. Biol. 213, 899-929] or Arg82 as postulated from an alternate model constructed primarily to accommodate the external point charge contribution to bacteriorhodopsin's opsin shift." @default.
• W2053185148 created "2016-06-24" @default.
• W2053185148 creator A5022666165 @default.
• W2053185148 creator A5037148437 @default.
• W2053185148 date "1991-03-19" @default.
• W2053185148 modified "2023-10-16" @default.
• W2053185148 title "Design of a helix-bundle cross-link: NMR and UV-visible spectroscopic analyses and molecular modeling of ring-oxidized retinals" @default.
• W2053185148 cites W1495982683 @default.
• W2053185148 cites W1509579025 @default.
• W2053185148 cites W1516690887 @default.
• W2053185148 cites W1532719100 @default.
• W2053185148 cites W1568427065 @default.
• W2053185148 cites W1587692148 @default.
• W2053185148 cites W1602954239 @default.
• W2053185148 cites W179754670 @default.
• W2053185148 cites W1964872214 @default.
• W2053185148 cites W1964955939 @default.
• W2053185148 cites W1966589956 @default.
• W2053185148 cites W1967619651 @default.
• W2053185148 cites W1967721238 @default.
• W2053185148 cites W1968402998 @default.
• W2053185148 cites W1969642737 @default.
• W2053185148 cites W1974064406 @default.
• W2053185148 cites W1977125557 @default.
• W2053185148 cites W197744617 @default.
• W2053185148 cites W1978811998 @default.
• W2053185148 cites W1985475076 @default.
• W2053185148 cites W1985980714 @default.
• W2053185148 cites W1992406804 @default.
• W2053185148 cites W1993844842 @default.
• W2053185148 cites W1995662488 @default.
• W2053185148 cites W1998092849 @default.
• W2053185148 cites W2002339883 @default.
• W2053185148 cites W2003802570 @default.
• W2053185148 cites W2006535314 @default.
• W2053185148 cites W2007742449 @default.
• W2053185148 cites W2010528272 @default.
• W2053185148 cites W2010594167 @default.
• W2053185148 cites W2011631323 @default.
• W2053185148 cites W2012254875 @default.
• W2053185148 cites W2013650899 @default.
• W2053185148 cites W2014687088 @default.
• W2053185148 cites W2015315677 @default.
• W2053185148 cites W2019641906 @default.
• W2053185148 cites W2020218612 @default.
• W2053185148 cites W2023401537 @default.
• W2053185148 cites W2025018393 @default.
• W2053185148 cites W2033208854 @default.
• W2053185148 cites W2045446885 @default.
• W2053185148 cites W2046219449 @default.
• W2053185148 cites W2050292589 @default.
• W2053185148 cites W2051121925 @default.
• W2053185148 cites W2051140533 @default.
• W2053185148 cites W2053426386 @default.
• W2053185148 cites W2059166011 @default.
• W2053185148 cites W2060001814 @default.
• W2053185148 cites W2061187728 @default.
• W2053185148 cites W2064709291 @default.
• W2053185148 cites W2065059675 @default.
• W2053185148 cites W2074770586 @default.
• W2053185148 cites W2077973224 @default.
• W2053185148 cites W2078493267 @default.
• W2053185148 cites W2078680169 @default.
• W2053185148 cites W2079241434 @default.
• W2053185148 cites W2083459965 @default.
• W2053185148 cites W2084720939 @default.
• W2053185148 cites W2086115599 @default.
• W2053185148 cites W2086447605 @default.
• W2053185148 cites W2086748378 @default.
• W2053185148 cites W2088668380 @default.
• W2053185148 cites W2090634877 @default.
• W2053185148 cites W2092226169 @default.
• W2053185148 cites W2110810808 @default.
• W2053185148 cites W2116498159 @default.
• W2053185148 cites W2117838041 @default.
• W2053185148 cites W2126280103 @default.
• W2053185148 cites W2128377068 @default.
• W2053185148 cites W2130653710 @default.
• W2053185148 cites W2313519577 @default.
• W2053185148 cites W2320054962 @default.
• W2053185148 cites W2321859908 @default.
• W2053185148 cites W2326629311 @default.
• W2053185148 cites W2331464269 @default.
• W2053185148 cites W2334539973 @default.
• W2053185148 cites W2338278417 @default.
• W2053185148 cites W2338295175 @default.
• W2053185148 cites W2339418965 @default.
• W2053185148 cites W2950951180 @default.
• W2053185148 cites W3004743473 @default.
• W2053185148 cites W3022921889 @default.
• W2053185148 cites W993137267 @default.
• W2053185148 doi "https://doi.org/10.1021/bi00225a035" @default.
• W2053185148 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/2007133" @default.
• W2053185148 hasPublicationYear "1991" @default.
• W2053185148 type Work @default.
• W2053185148 sameAs 2053185148 @default.
• W2053185148 citedByCount "2" @default.
• W2053185148 crossrefType "journal-article" @default.

• next