-
1
-
-
0031050888
-
-
T. Gudemann, T. Schoneberg, G. Schultz, Annu. Rev. Neurosci. 1997, 20, 399-427.
-
(1997)
Annu. Rev. Neurosci.
, vol.20
, pp. 399-427
-
-
Gudemann, T.1
Schoneberg, T.2
Schultz, G.3
-
2
-
-
0035385140
-
-
For recent reviews, see: a) R. R. Rando, Chem. Rev. 2001, 101, 1881-1896;
-
(2001)
Chem. Rev.
, vol.101
, pp. 1881-1896
-
-
Rando, R.R.1
-
3
-
-
0034982559
-
-
b) K. J. McBee, K. Palczewski, W. Baehr, D. R. Pepperberg, Prog. Retinal. Eye Res. 2001, 20, 469-529.
-
(2001)
Prog. Retinal. Eye Res.
, vol.20
, pp. 469-529
-
-
McBee, K.J.1
Palczewski, K.2
Baehr, W.3
Pepperberg, D.R.4
-
4
-
-
0026091595
-
-
W. R. Schoenlein, A. L. Peteann, A. R. Mathies, C. V. Shank, Science 1991, 254, 412-415.
-
(1991)
Science
, vol.254
, pp. 412-415
-
-
Schoenlein, W.R.1
Peteann, A.L.2
Mathies, A.R.3
Shank, C.V.4
-
5
-
-
26744449806
-
-
L. Stryer, J. Biol. Chem. 1990, 265 266, 10711-10714.
-
(1990)
J. Biol. Chem.
, vol.265-266
, pp. 10711-10714
-
-
Stryer, L.1
-
6
-
-
0343177634
-
-
P. T. Sakmar, R. R. Franke, H. G. Khorana, Proc. Natl. Acad. Sci. USA 1989, 86, 8309-8313.
-
(1989)
Proc. Natl. Acad. Sci. USA
, vol.86
, pp. 8309-8313
-
-
Sakmar, P.T.1
Franke, R.R.2
Khorana, H.G.3
-
7
-
-
0034604451
-
-
a) K. Palczewski, T. Kumasaka, T. Hori, C. A. Behnke, H. Motoshima, B. A. Fox, I. Le Trong, D. C. Teller, T. Okada, R. E. Stenkamp, M. Yamamoto, M. Miyano, Science 2000, 289, 739-745;
-
(2000)
Science
, vol.289
, pp. 739-745
-
-
Palczewski, K.1
Kumasaka, T.2
Hori, T.3
Behnke, C.A.4
Motoshima, H.5
Fox, B.A.6
Le Trong, I.7
Teller, D.C.8
Okada, T.9
Stenkamp, R.E.10
Yamamoto, M.11
Miyano, M.12
-
9
-
-
0035800032
-
-
c) D. C. Teller, T. Okada, C. A. Behnke, K. Palczewski, R. Stenkamp, Biochemistry 2001, 40, 7761-7762.
-
(2001)
Biochemistry
, vol.40
, pp. 7761-7762
-
-
Teller, D.C.1
Okada, T.2
Behnke, C.A.3
Palczewski, K.4
Stenkamp, R.5
-
10
-
-
26744464820
-
-
a) W. Gärtner, Angew. Chem. 2001, 113, 3065-3069; Angew. Chem. Int. Ed. 2001, 40, 2977-2981;
-
(2001)
Angew. Chem.
, vol.113
, pp. 3065-3069
-
-
Gärtner, W.1
-
11
-
-
0035902789
-
-
a) W. Gärtner, Angew. Chem. 2001, 113, 3065-3069; Angew. Chem. Int. Ed. 2001, 40, 2977-2981;
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 2977-2981
-
-
-
13
-
-
0041925521
-
-
13C-labeled 11-cis-retinal confirmed the 6-s-cis conformation of the chromophore: A. F. L. Creemers, S. Kiihne, P. H. M. Bovee-Geurts, W. J. DeGrip, J. Lugtenburg, H. J. M. Groot, Proc. Natl. Acad. Sci. USA 2002, 99, 9101-9106.
-
(2000)
Nature
, vol.405
, pp. 810-813
-
-
Gröbner, G.1
Burnett, I.J.2
Glaubitz, C.3
Choi, G.4
Mason, A.J.5
Watts, A.6
-
14
-
-
0037047148
-
-
13C-labeled 11-cis-retinal confirmed the 6-s-cis conformation of the chromophore: A. F. L. Creemers, S. Kiihne, P. H. M. Bovee-Geurts, W. J. DeGrip, J. Lugtenburg, H. J. M. Groot, Proc. Natl. Acad. Sci. USA 2002, 99, 9101-9106.
-
(2002)
Proc. Natl. Acad. Sci. USA
, vol.99
, pp. 9101-9106
-
-
Creemers, A.F.L.1
Kiihne, S.2
Bovee-Geurts, P.H.M.3
DeGrip, W.J.4
Lugtenburg, J.5
Groot, H.J.M.6
-
16
-
-
0035476603
-
-
The twisted polyene chain of 11-cis-retinal 1 within the binding pocket is intrinsically chiral. The absolute sense of twist around the 6-s-cis bond has been determined as negative with the use of locked synthetic retinal analogues; see: Y. Fujimoto, J. Ishihara, S. Maki, N. Fujioka, T. Wang, T. Furuta, N. Fishkin, B. Borham, N. Berova, K. Nakanishi, Chem. Eur. J. 2001, 7, 4198-4204. See also the discussion in the same paper on the positive helicity about the 12-s-bond.
-
(2001)
Chem. Eur. J.
, vol.7
, pp. 4198-4204
-
-
Fujimoto, Y.1
Ishihara, J.2
Maki, S.3
Fujioka, N.4
Wang, T.5
Furuta, T.6
Fishkin, N.7
Borham, B.8
Berova, N.9
Nakanishi, K.10
-
17
-
-
0024617333
-
-
A. Albeck, N. Friedman, M. Ottolenghi, M. Sheves, C. M. Einterz, S. J. Hug, J. W. Lewis, D. S. Kliger, Biophys. J. 1989, 55, 233-241.
-
(1989)
Biophys. J.
, vol.55
, pp. 233-241
-
-
Albeck, A.1
Friedman, N.2
Ottolenghi, M.3
Sheves, M.4
Einterz, C.M.5
Hug, S.J.6
Lewis, J.W.7
Kliger, D.S.8
-
18
-
-
0035854788
-
-
G.-F. Jang, V. Kuksa, S. Filipek, F. Barti, E. Ritter, M. Gelb, P. K. Hofmann, K. Palczewski, J. Biol. Chem. 2001, 276, 26148-26153.
-
(2001)
J. Biol. Chem.
, vol.276
, pp. 26148-26153
-
-
Jang, G.-F.1
Kuksa, V.2
Filipek, S.3
Barti, F.4
Ritter, E.5
Gelb, M.6
Hofmann, P.K.7
Palczewski, K.8
-
19
-
-
0034705612
-
-
Recent photoaffinity labeling studies using the photolysis of diazo groups attached to the hydrophobic ring appear to be consistent with this proposal: B. Borhan, M. L. Souto, H. Imai, Y. Shichida, K. Nakanishi, Science 2000, 288, 2209-2212.
-
(2000)
Science
, vol.288
, pp. 2209-2212
-
-
Borhan, B.1
Souto, M.L.2
Imai, H.3
Shichida, Y.4
Nakanishi, K.5
-
20
-
-
0029148981
-
-
Substitution of the retinal side chain at C8 is uncommon. For previous studies on the interaction of a trans-retinal that was modified at C8 with bacteriorhodopsin, which is the protein of the purple membrane of Halobacterium salinarum; see: a) A. R. de Lera, B. Iglesias, J. Rodríguez, R. Alvarez, S. López, J. Villanueva, E. Padrós, J. Am. Chem. Soc. 1995, 117, 8220-8231;
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 8220-8231
-
-
De Lera, A.R.1
Iglesias, B.2
Rodríguez, J.3
Alvarez, R.4
López, S.5
Villanueva, J.6
Padrós, E.7
-
21
-
-
33748648236
-
-
b) 6-s-cis-locked retinoids with a ring that spans the C18 and C8 positions have been described: Y. Katsuta, Y. Aoyama, H. Ozone, A. Wada, M. Ito, J. Chem. Soc. Perkin Trans. 1 1997, 1405-1410;
-
(1997)
J. Chem. Soc. Perkin Trans. 1
, pp. 1405-1410
-
-
Katsuta, Y.1
Aoyama, Y.2
Ozone, H.3
Wada, A.4
Ito, M.5
-
22
-
-
0029920050
-
-
c) Liu has also described retinals fluorinated at C8, see: C. J. Simmons, L. U. Colmenares, R. S. H. Liu, Tetrahedron Lett. 1996, 37, 4103-4104,
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 4103-4104
-
-
Simmons, C.J.1
Colmenares, L.U.2
Liu, R.S.H.3
-
28
-
-
33847086004
-
-
b )E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc. 1980, 102, 3298-3299;
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 3298-3299
-
-
Negishi, E.1
Valente, L.F.2
Kobayashi, M.3
-
29
-
-
0000509942
-
-
c) E. Negishi, A. O. King, W. L. Klima, W. Patterson, A. Silveira, J. Org. Chem. 1980, 45, 2526-2528;
-
(1980)
J. Org. Chem.
, vol.45
, pp. 2526-2528
-
-
Negishi, E.1
King, A.O.2
Klima, W.L.3
Patterson, W.4
Silveira, A.5
-
30
-
-
33845557644
-
-
d) C. L. Rand, D. E. Van Harn, M. W. Moore, E. Negishi, J. Org. Chem, 1981, 46, 4093-4096;
-
(1981)
J. Org. Chem.
, vol.46
, pp. 4093-4096
-
-
Rand, C.L.1
Van Harn, D.E.2
Moore, M.W.3
Negishi, E.4
-
37
-
-
0032511007
-
-
c) B. Domínguez, B. Iglesias, A. R. de Lera, J. Org. Chem. 1998, 63, 4135-4139.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4135-4139
-
-
Domínguez, B.1
Iglesias, B.2
De Lera, A.R.3
-
39
-
-
0040785991
-
-
F. Derguini, V. Balog-Nair, K. Nakanishi, Tetrahedron Lett. 1979, 20, 4899-4902.
-
(1979)
Tetrahedron Lett.
, vol.20
, pp. 4899-4902
-
-
Derguini, F.1
Balog-Nair, V.2
Nakanishi, K.3
-
41
-
-
0035861718
-
-
Y. Pazos, B. Iglesias, A. R. de Lera, J. Org. Chem. 2001, 66, 8483-8489.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8483-8489
-
-
Pazos, Y.1
Iglesias, B.2
De Lera, A.R.3
-
42
-
-
33845281635
-
-
J. Uenishi, J.-M. Beau, R. W. Armstrong, Y. Kishi, J. Am. Chem. Soc. 1987, 109, 4756-4768.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 4756-4768
-
-
Uenishi, J.1
Beau, J.-M.2
Armstrong, R.W.3
Kishi, Y.4
-
43
-
-
85027851932
-
-
D. H. R. Barton, M. Chen, J. C. Jaszberenyi, D. K. Taylor, Org. Synth. 1997, 74, 101-107.
-
(1997)
Org. Synth.
, vol.74
, pp. 101-107
-
-
Barton, D.H.R.1
Chen, M.2
Jaszberenyi, J.C.3
Taylor, D.K.4
-
44
-
-
0041807380
-
-
W. P. Griffith, S. V. Ley, G. P. Withcombe, A. D. White, J. Chem. Soc. Chem. Commun. 1987, 1625-1627.
-
(1987)
J. Chem. Soc. Chem. Commun.
, pp. 1625-1627
-
-
Griffith, W.P.1
Ley, S.V.2
Withcombe, G.P.3
White, A.D.4
-
45
-
-
0023280801
-
-
A. Hosoda, T. Taguchi, Y. Kobayashi, Tetrahedron Lett. 1987, 28, 65-68.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 65-68
-
-
Hosoda, A.1
Taguchi, T.2
Kobayashi, Y.3
-
47
-
-
0000300950
-
-
C. J. Simmons, R. S. H. Liu, M. Denny, K. Seff, Acta Crystallogr Sect. B 1981, 37, 2197-2205;) C. J. Simmons, A. E. Asato, R. S. H. Liu, Acta Crystallogr. Sect. C 1986, 42, 711-715, 1558-1563.
-
(1981)
Acta Crystallogr. Sect. B
, vol.37
, pp. 2197-2205
-
-
Simmons, C.J.1
Liu, R.S.H.2
Denny, M.3
Seff, K.4
-
48
-
-
0040411774
-
-
C. J. Simmons, R. S. H. Liu, M. Denny, K. Seff, Acta Crystallogr Sect. B 1981, 37, 2197-2205;) C. J. Simmons, A. E. Asato, R. S. H. Liu, Acta Crystallogr. Sect. C 1986, 42, 711-715, 1558-1563.
-
(1986)
Acta Crystallogr. Sect. C
, vol.42
, pp. 711-715
-
-
Simmons, C.J.1
Asato, A.E.2
Liu, R.S.H.3
-
49
-
-
0000116680
-
-
R. Gilardi, Karle, L. I. J. Karle, W. Sperling, Nature 1971, 232, 187-189.
-
(1971)
Nature
, vol.232
, pp. 187-189
-
-
Gilardi, R.1
Karle2
Karle, L.I.J.3
Sperling, W.4
-
50
-
-
0346819141
-
-
note
-
However, upon binding the apoproteins, a selection of 6-s-cis or 6-s-trans conformations is made by the receptor depending upon the tolerance of its binding pocket (i.e., 6-s-cis for 11-cis-retinal in rhodopsin ref. [6], and 6-s-trans for trans-retinal in bacteriorhodopsin ref. [34], which is the protein of the purple membrane of Halobacterium salinarium).
-
-
-
-
51
-
-
0033609904
-
-
a) H. Leucke, B. Schobert, H.-T. Richter, J.-P. Cartailler, J. K. Lanyi, J. Mol. Biol. 1999, 291, 899-911;
-
(1999)
J. Mol. Biol.
, vol.291
, pp. 899-911
-
-
Leucke, H.1
Schobert, B.2
Richter, H.-T.3
Cartailler, J.-P.4
Lanyi, J.K.5
-
52
-
-
0034632821
-
-
b) A. Royant, K. Edman, T. Ursby, E. Pebay-Peyroula, E. M. Landau, R. Neutze, Nature 2000, 406, 645-648;
-
(2000)
Nature
, vol.406
, pp. 645-648
-
-
Royant, A.1
Edman, K.2
Ursby, T.3
Pebay-Peyroula, E.4
Landau, E.M.5
Neutze, R.6
-
53
-
-
0342646933
-
-
c) H. J. Sass, G. Büdlt, R. Gessenich, D. Hehn, D. Neff, R. Schlessinger, J. Berendzen, P. Ormos, Nature 2000, 406, 649-652.
-
(2000)
Nature
, vol.406
, pp. 649-652
-
-
Sass, H.J.1
Büdlt, G.2
Gessenich, R.3
Hehn, D.4
Neff, D.5
Schlessinger, R.6
Berendzen, J.7
Ormos, P.8
-
55
-
-
0001756583
-
-
for other ab initio studies of the same group on 11-cis-retinal and its Schiff base, see: b) F. Terstegen, V. Buss, THEOCHEM 1998, 430, 209-218;
-
(1998)
THEOCHEM
, vol.430
, pp. 209-218
-
-
Terstegen, F.1
Buss, V.2
-
56
-
-
0001313251
-
-
c) V. Buss, K. Kolster, F. Terstegen, R. Vahrenhorst, Angew. Chem. 1998, 110, 1997-2000; Angew. Chem. Int. Ed. 1998, 37, 1893-1895;
-
(1998)
Angew. Chem.
, vol.110
, pp. 1997-2000
-
-
Buss, V.1
Kolster, K.2
Terstegen, F.3
Vahrenhorst, R.4
-
57
-
-
0344972891
-
-
c) V. Buss, K. Kolster, F. Terstegen, R. Vahrenhorst, Angew. Chem. 1998, 110, 1997-2000; Angew. Chem. Int. Ed. 1998, 37, 1893-1895;
-
(1998)
Angew. Chem. Int. Ed.
, vol.37
, pp. 1893-1895
-
-
-
58
-
-
0347449817
-
-
d) V. Buss, O. Weingart, M. Sugihara, Angew. Chem. 2000, 112, 2895-2898; Angew. Chem. Int. Ed. 2000, 39, 2784-2786.
-
(2000)
Angew. Chem.
, vol.112
, pp. 2895-2898
-
-
Buss, V.1
Weingart, O.2
Sugihara, M.3
-
59
-
-
0039000044
-
-
d) V. Buss, O. Weingart, M. Sugihara, Angew. Chem. 2000, 112, 2895-2898; Angew. Chem. Int. Ed. 2000, 39, 2784-2786.
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 2784-2786
-
-
-
60
-
-
26744474577
-
-
13C NMR was also interpreted as arising from the conformational interconversion of the ring side chain: K. Müllen, H. Schmickler, B. Frei, H. R. Wolf, Tetrahedron Lett. 1986, 27, 477-480.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 477-480
-
-
Müllen, K.1
Schmickler, H.2
Frei, B.3
Wolf, H.R.4
-
61
-
-
84986512474
-
-
B. R. Brooks, E. R. Bruccoleri, B. D. Olafson, D. J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 1983, 4, 187-217.
-
(1983)
J. Comput. Chem.
, vol.4
, pp. 187-217
-
-
Brooks, B.R.1
Bruccoleri, E.R.2
Olafson, B.D.3
States, D.J.4
Swaminathan, S.5
Karplus, M.6
-
62
-
-
0344804875
-
-
R. Hubbard, P. K. Brown, D. Bownds, Methods Enzymol. 1971, 18, 628-653.
-
(1971)
Methods Enzymol.
, vol.18
, pp. 628-653
-
-
Hubbard, R.1
Brown, P.K.2
Bownds, D.3
-
63
-
-
0037065669
-
-
I. Szundi, A.R. de Lera, Y. Pazos, R. Alvarez, M. Oliana, M. Sheves, J. Lewis, D. S. Kliger, Biochemistry 2002, 41, 2028-2035.
-
(2002)
Biochemistry
, vol.41
, pp. 2028-2035
-
-
Szundi, I.1
De Lera, A.R.2
Pazos, Y.3
Alvarez, R.4
Oliana, M.5
Sheves, M.6
Lewis, J.7
Kliger, D.S.8
-
64
-
-
0036286654
-
-
a) T. Simonson, G. Archontis, M. Karplus, Acc. Chem. Res. 2002, 35, 430-437;
-
(2002)
Acc. Chem. Res.
, vol.35
, pp. 430-437
-
-
Simonson, T.1
Archontis, G.2
Karplus, M.3
-
65
-
-
0036280661
-
-
b) J. Åquist, V. B. Luzhkov, B. O. Brandsdal, Acc. Chem. Res. 2002, 35, 358-365.
-
(2002)
Acc. Chem. Res.
, vol.35
, pp. 358-365
-
-
Åquist, J.1
Luzhkov, V.B.2
Brandsdal, B.O.3
-
66
-
-
0344778061
-
-
W. C. Still, A. Tempczyk, R. C. Hawley, T. J. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6127-6129
-
-
Still, W.C.1
Tempczyk, A.2
Hawley, R.C.3
Hendrickson, T.J.4
-
67
-
-
0026416668
-
-
K. A. Sharp, A. Nicholls, R. F. Fine, B. Honig, Science 1991, 252,106-109.
-
(1991)
Science
, vol.252
, pp. 106-109
-
-
Sharp, K.A.1
Nicholls, A.2
Fine, R.F.3
Honig, B.4
-
68
-
-
0347449813
-
-
InsightII, Builder and Biopolymer are trademarks of Accelrys, Inc. San Diego, CA (USA)
-
InsightII, Builder and Biopolymer are trademarks of Accelrys, Inc. San Diego, CA (USA).
-
-
-
|