-
3
-
-
18144447465
-
-
(a) Yoshikawa, S.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yamashita, E.; Inoue, N.; Yao, M.; Fei, M. J.; Libeu, C. P.; Mizushima, T.; Yamaguchi, H.; Tomizaki, T.; Tsukihara, T. Science 1998, 280, 1723-1729.
-
(1998)
Science
, vol.280
, pp. 1723-1729
-
-
Yoshikawa, S.1
Shinzawa-Itoh, K.2
Nakashima, R.3
Yaono, R.4
Yamashita, E.5
Inoue, N.6
Yao, M.7
Fei, M.J.8
Libeu, C.P.9
Mizushima, T.10
Yamaguchi, H.11
Tomizaki, T.12
Tsukihara, T.13
-
4
-
-
0030886203
-
-
(b) Ostermeier, C.; Harrenga, A.; Ermler, U.; Michel, H. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10547-10553.
-
(1997)
Proc. Natl. Acad. Sci. U.S.A.
, vol.94
, pp. 10547-10553
-
-
Ostermeier, C.1
Harrenga, A.2
Ermler, U.3
Michel, H.4
-
5
-
-
0034678612
-
-
(c) Soulimane, T.; Buse, G.; Bourenkov, G. P.; Bartunik, H. D.; Huber, R.; Than, M. E. EMBO J. 2000, 19, 1766-1776.
-
(2000)
EMBO J.
, vol.19
, pp. 1766-1776
-
-
Soulimane, T.1
Buse, G.2
Bourenkov, G.P.3
Bartunik, H.D.4
Huber, R.5
Than, M.E.6
-
6
-
-
60549100318
-
-
PDB ID: 2zxw
-
PDB ID: 2zxw; Aoyama, H.; Muramoto, K.; Shinzawa-Itoh, K.; Hirata, K.; Yamashita, E.; Tsukihara, T.; Ogura, T.; Yoshikawa, S. Proc. Nat. Acad. Sci. U.S.A. 2009, 106, 2165-2169.
-
(2009)
Proc. Nat. Acad. Sci. U.S.A.
, vol.106
, pp. 2165-2169
-
-
Aoyama, H.1
Muramoto, K.2
Shinzawa-Itoh, K.3
Hirata, K.4
Yamashita, E.5
Tsukihara, T.6
Ogura, T.7
Yoshikawa, S.8
-
7
-
-
0032493345
-
-
Proshlyakov, D. A.; Pressler, M. A.; Babcock, G. T. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 8020-8025.
-
(1998)
Proc. Natl. Acad. Sci. U.S.A.
, vol.95
, pp. 8020-8025
-
-
Proshlyakov, D.A.1
Pressler, M.A.2
Babcock, G.T.3
-
9
-
-
0032558999
-
-
Sucheta, A.; Szundi, I.; Einarsdóttir, Ó. Biochemistry 1998, 37, 17905-17914.
-
(1998)
Biochemistry
, vol.37
, pp. 17905-17914
-
-
Sucheta, A.1
Szundi, I.2
Einarsdóttir, Ó.3
-
10
-
-
0034233381
-
-
(a) Blomberg, M. R. A.; Siegbahn, P. E. M.; Babcock, G. T.; Wikström, M. K. F. J. Inorg. Biochem. 2000, 80, 261-269.
-
(2000)
J. Inorg. Biochem.
, vol.80
, pp. 261-269
-
-
Blomberg, M.R.A.1
Siegbahn, P.E.M.2
Babcock, G.T.3
Wikström, M.K.F.4
-
11
-
-
1942472143
-
-
(b) Svistunenko, D. A.; Wilson, M. T.; Cooper, C. E. Biochim. Biophys. Acta 2004, 1655, 372-380.
-
(2004)
Biochim. Biophys. Acta
, vol.1655
, pp. 372-380
-
-
Svistunenko, D.A.1
Wilson, M.T.2
Cooper, C.E.3
-
12
-
-
0034711407
-
-
(c) Proshlyakov, D. A.; Pressler, M. A.; DeMaso, C.; Leykam, J. F.; Dewitt, D. L.; Babcock, G. T. Science 2000, 290, 1588-1591.
-
(2000)
Science
, vol.290
, pp. 1588-1591
-
-
Proshlyakov, D.A.1
Pressler, M.A.2
DeMaso, C.3
Leykam, J.F.4
Dewitt, D.L.5
Babcock, G.T.6
-
13
-
-
2242476596
-
-
(d) Tomson, F.; Bailey, J. A.; Gennis, R. B.; Unkefer, C. J.; Li, Z. H.; Silks, L. A.; Martinez, R. A.; Donohoe, R. J.; Dyer, R. B.; Woodruff, W. H. Biochemistry 2002, 41, 14383-14390.
-
(2002)
Biochemistry
, vol.41
, pp. 14383-14390
-
-
Tomson, F.1
Bailey, J.A.2
Gennis, R.B.3
Unkefer, C.J.4
Li, Z.H.5
Silks, L.A.6
Martinez, R.A.7
Donohoe, R.J.8
Dyer, R.B.9
Woodruff, W.H.10
-
14
-
-
0042307434
-
-
(e) Nyquist, R. M.; Heitbrink, D.; Bolwien, C.; Gennis, R. B.; Heberle, J. Proc. Natl. Acad. Sci. U.S.A 2003, 100, 8715-8720.
-
(2003)
Proc. Natl. Acad. Sci. U.S.A
, vol.100
, pp. 8715-8720
-
-
Nyquist, R.M.1
Heitbrink, D.2
Bolwien, C.3
Gennis, R.B.4
Heberle, J.5
-
17
-
-
0037181057
-
-
(b) Cappuccio, J. A.; Ayala, I.; Elliott, G. I.; Szundi, I.; Lewis, J.; Konopelski, J. P.; Barry, B. A.; Einarsdóttir, Ó. J. Am. Chem. Soc. 2002, 124, 1750-1760
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 1750-1760
-
-
Cappuccio, J.A.1
Ayala, I.2
Elliott, G.I.3
Szundi, I.4
Lewis, J.5
Konopelski, J.P.6
Barry, B.A.7
Einarsdóttir, Ó.8
-
18
-
-
33947623768
-
-
(c) Landaverry, Y. R.; White, K. N.; Olmstead, M. M.; Einarsdóttir, Ó; Konopelski, J. P. Heterocycles 2006, 70, 147-152.
-
(2006)
Heterocycles
, vol.70
, pp. 147-152
-
-
Landaverry, Y.R.1
White, K.N.2
Olmstead, M.M.3
Einarsdóttir, Ó.4
Konopelski, J.P.5
-
19
-
-
34547593905
-
-
(d) White, K. N.; Sen, I.; Szundi, I.; Landaverry, Y. R.; Bria, L. E.; Konopelski, J. P.; Olmstead, M. M.; Einarsdóttir, Ó. Chem. Commun. 2007, 31, 3252-3254.
-
(2007)
Chem. Commun.
, vol.31
, pp. 3252-3254
-
-
White, K.N.1
Sen, I.2
Szundi, I.3
Landaverry, Y.R.4
Bria, L.E.5
Konopelski, J.P.6
Olmstead, M.M.7
Einarsdóttir, Ó.8
-
20
-
-
70350705130
-
-
Masters Thesis, University of California Santa Cruz
-
Moore, E. M., Masters Thesis, University of California Santa Cruz, 2000.
-
(2000)
-
-
Moore, E.M.1
-
22
-
-
0034699305
-
-
Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027-3029.
-
(2000)
Org. Lett.
, vol.2
, pp. 3027-3029
-
-
Kawasaki, T.1
Enoki, H.2
Matsumura, K.3
Ohyama, M.4
Inagawa, M.5
Sakamoto, M.6
-
23
-
-
67650566924
-
-
Koreeda, T.; Kochi, T.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 7238-7239.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 7238-7239
-
-
Koreeda, T.1
Kochi, T.2
Kakiuchi, F.3
-
24
-
-
33745596385
-
-
Shieh, W. -C.; Xue, S.; McKenna, J.; Prasad, K.; Repič, O.; Blacklock, T. Tetrahedron Lett. 2006, 47, 5645-5648.
-
(2006)
Tetrahedron Lett.
, vol.47
, pp. 5645-5648
-
-
Shieh, W.C.1
Xue, S.2
McKenna, J.3
Prasad, K.4
Repič, O.5
Blacklock, T.6
-
25
-
-
32344436731
-
-
Hart, M. E.; Suchland, K. L.; Miyakawa, M.; Bunzow, J. R.; Grandy, D. K.; Scanlan, T. S. J. Med. Chem. 2006, 49, 1101-1112.
-
(2006)
J. Med. Chem.
, vol.49
, pp. 1101-1112
-
-
Hart, M.E.1
Suchland, K.L.2
Miyakawa, M.3
Bunzow, J.R.4
Grandy, D.K.5
Scanlan, T.S.6
-
28
-
-
34547621822
-
-
(b) Jiang, Q; Jiang, D; Jiang, Y.; Fu, H.; Zhao, Y. Synlett 2007, 1836-1842.
-
(2007)
Synlett
, pp. 1836-1842
-
-
Jiang, Q.1
Jiang, D.2
Jiang, Y.3
Fu, H.4
Zhao, Y.5
-
29
-
-
64249097478
-
-
(c) Zhu, L.; Li, G.; Luo, L.; Guo, P.; Lan, J.; Youet, J. J. Org. Chem. 2009, 74, 2200-2202.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 2200-2202
-
-
Zhu, L.1
Li, G.2
Luo, L.3
Guo, P.4
Lan, J.5
Youet, J.6
-
30
-
-
0032493017
-
-
(a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2941-2944
-
-
Lam, P.Y.S.1
Clark, C.G.2
Saubern, S.3
Adams, J.4
Winters, M.P.5
Chan, D.M.T.6
Combs, A.7
-
31
-
-
1642480209
-
-
(b) Lan, J. -B.; Chen, L.; Yu, X.-Q.; You, J.-S.; Xie, R.-G. Chem. Commun. 2004, 188-189.
-
(2004)
Chem. Commun.
, pp. 188-189
-
-
Lan, J.B.1
Chen, L.2
Yu, X.-Q.3
You, J.-S.4
Xie, R.-G.5
-
32
-
-
70350707041
-
-
Ph.D. Thesis, University of California Santa Cruz
-
Gerstenberger, B. S., Ph.D. Thesis, University of California Santa Cruz , 2007
-
(2007)
-
-
Gerstenberger, B.S.1
-
33
-
-
34247182651
-
-
Poriel, C.; Lachia, M.; Wilson, C.; Davies, J. R.; Moody, C. J. J. Org. Chem. 2007, 72, 2978-2987.
-
(2007)
J. Org. Chem.
, vol.72
, pp. 2978-2987
-
-
Poriel, C.1
Lachia, M.2
Wilson, C.3
Davies, J.R.4
Moody, C.J.5
-
34
-
-
0035810387
-
-
Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032.
-
(2001)
Org. Lett.
, vol.3
, pp. 1029-1032
-
-
Decicco, C.P.1
Song, Y.2
Evans, D.A.3
-
36
-
-
70350711582
-
-
Increasing the arylboronic acid to histidine ratio to 1.4:1 does not improve the yield
-
Increasing the arylboronic acid to histidine ratio to 1.4:1 does not improve the yield.
-
-
-
-
38
-
-
45549083040
-
-
Park, Y. H.; Ahn, H. R.; Canturk, B.; Jeon, S. I.; Lee, S.; Kang, H.; Molander, G. A.; Ham, J. Org. Lett. 2008, 10, 1215-1218.
-
(2008)
Org. Lett.
, vol.10
, pp. 1215-1218
-
-
Park, Y.H.1
Ahn, H.R.2
Canturk, B.3
Jeon, S.I.4
Lee, S.5
Kang, H.6
Molander, G.A.7
Ham, J.8
-
39
-
-
24144447839
-
-
Skaff, O.; Jolliffe, K. A.; Hutton, C. A. J. Org. Chem. 2005, 70, 7353-7363.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 7353-7363
-
-
Skaff, O.1
Jolliffe, K.A.2
Hutton, C.A.3
-
41
-
-
41649111112
-
-
Ginisty, M.; Roy, M.-N.; Charette, A. B. J. Org. Chem. 2008, 73, 2542-2547.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 2542-2547
-
-
Ginisty, M.1
Roy, M.-N.2
Charette, A.B.3
-
42
-
-
5644298630
-
-
While this 10% impurity of free phenol was removed to obtain a pure sample of 23, its presence posed no problems for the production of 24
-
Nicolaou, K. C.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Bella, M.; Snyder, S. A. J. Am. Chem. Soc. 2004, 126, 12888-12896. While this 10% impurity of free phenol was removed to obtain a pure sample of 23, its presence posed no problems for the production of 24.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 12888-12896
-
-
Nicolaou, K.C.1
Chen, D.Y.-K.2
Huang, X.3
Ling, T.4
Bella, M.5
Snyder, S.A.6
-
43
-
-
0033593395
-
-
Akaji, K.; Hayashi, Y.; Kiso, Y.; Kuriyama, N. J. Org. Chem. 1999, 64, 405-411.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 405-411
-
-
Akaji, K.1
Hayashi, Y.2
Kiso, Y.3
Kuriyama, N.4
-
44
-
-
70350718615
-
-
Solvent and water molecules omitted for clarity
-
Solvent and water molecules omitted for clarity.
-
-
-
-
45
-
-
29844456385
-
-
DFTcalculations on simplemodel systems put the BDA at 42.5°, very close to the native enzyme BDA. Most X-ray structures, including our own previous work, suffer from intermolecular hydrogen bonds that likely perturb the fundamental BDA; in our laboratory we have documented BDAs ranging from -25.7° to -36.3°. By contrast, the structure of 24 appears devoid of serious intermolecular interactions. Hence, this molecule affords the best experimental evidence for the intrinsic BDA of the biaryl cofactor
-
DFTcalculations on simplemodel systems ( Pratt, D.A.; Pesavento, R. P.; van der Donk, W. A. Org. Lett. 2005, 7, 2735-2738.) put the BDA at 42.5°, very close to the native enzyme BDA. Most X-ray structures, including our own previous work, suffer from intermolecular hydrogen bonds that likely perturb the fundamental BDA; in our laboratory we have documented BDAs ranging from -25.7° to -36.3°. By contrast, the structure of 24 appears devoid of serious intermolecular interactions. Hence, this molecule affords the best experimental evidence for the intrinsic BDA of the biaryl cofactor.
-
(2005)
Org. Lett.
, vol.7
, pp. 2735-2738
-
-
Pratt, D.A.1
Pesavento, R.P.2
Van Der Donk, W.A.3
-
46
-
-
70350715727
-
-
Macromodel v9.0.014 was used for the calculations. The Amber* force field was employed, dielectric = 80, with a PRCG minimization method
-
Macromodel v9.0.014 was used for the calculations. The Amber* force field was employed, dielectric = 80, with a PRCG minimization method.
-
-
-
-
47
-
-
67049086176
-
-
Qin, L.; Liu, J.; Mills, D. A.; Proshlyakov, D. A.; Hiser, C.; Ferguson-Miller, S. Biochemistry 2009, 48, 5121-5130.
-
(2009)
Biochemistry
, vol.48
, pp. 5121-5130
-
-
Qin, L.1
Liu, J.2
Mills, D.A.3
Proshlyakov, D.A.4
Hiser, C.5
Ferguson-Miller, S.6
|