-
1
-
-
0022992561
-
-
(a) Tramontano, A.; Janda, K.; Lerner, R.A. Science 1986, 234, 1566-1570.
-
(1986)
Science
, vol.234
, pp. 1566-1570
-
-
Tramontano, A.1
Janda, K.2
Lerner, R.A.3
-
2
-
-
0022991435
-
-
(b) Pollack, S.J.; Jacobs, J.W.; Schultz, P.G. Science 1986, 234, 1570-1573.
-
(1986)
Science
, vol.234
, pp. 1570-1573
-
-
Pollack, S.J.1
Jacobs, J.W.2
Schultz, P.G.3
-
3
-
-
0025730616
-
-
(a) Lerner, R.A.; Benkovic, S.J.; Schultz, P.G. Science 1991, 252, 659.
-
(1991)
Science
, vol.252
, pp. 659
-
-
Lerner, R.A.1
Benkovic, S.J.2
Schultz, P.G.3
-
6
-
-
0028763728
-
-
(a) Haynes, M.R.; Stura, E.A.; Hilvert D.; Wilson, I.A. Science 1994, 263, 646.
-
(1994)
Science
, vol.263
, pp. 646
-
-
Haynes, M.R.1
Stura, E.A.2
Hilvert, D.3
Wilson, I.A.4
-
7
-
-
0028027058
-
-
(b) Zhou, G.W.; Guo, J.; Fetterick, R.J.; Scanlon, T.S. Science 1994, 265, 1059.
-
(1994)
Science
, vol.265
, pp. 1059
-
-
Zhou, G.W.1
Guo, J.2
Fetterick, R.J.3
Scanlon, T.S.4
-
8
-
-
0028773154
-
-
(c) Golinelli-Pimpaneau, B.; Gigant, B.; Bizebard, T.; Navaza, J.; Saludjian, P.; Zemel, R.; Tawfik, D.S.; Eshhar, Z.; Green, B.S.; Knossow, M. Structure 1994, 2, 175.
-
(1994)
Structure
, vol.2
, pp. 175
-
-
Golinelli-Pimpaneau, B.1
Gigant, B.2
Bizebard, T.3
Navaza, J.4
Saludjian, P.5
Zemel, R.6
Tawfik, D.S.7
Eshhar, Z.8
Green, B.S.9
Knossow, M.10
-
9
-
-
33748223514
-
-
(a) Reymond, J.-L.; Rebec, J.-L.; Lerner, R.A. Angew. Chem., Int. Ed. Engl. 1994, 33, 475.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 475
-
-
Reymond, J.-L.1
Rebec, J.-L.2
Lerner, R.A.3
-
10
-
-
0028297465
-
-
(b) Shevlin, C.G.; Hilton, S.; Janda, K.D. Bioorg. Med. Chem. Lett. 1994, 4, 297.
-
(1994)
Bioorg. Med. Chem. Lett.
, vol.4
, pp. 297
-
-
Shevlin, C.G.1
Hilton, S.2
Janda, K.D.3
-
11
-
-
0028904199
-
-
For a preliminary report of this work, see: Sinha, S.C., Keinan, E. J. Am. Chem. Soc. 1995, 117, 3653.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 3653
-
-
Sinha, S.C.1
Keinan, E.2
-
12
-
-
0039495882
-
-
note
-
As all reagents used in the synthesis are achiral, the only source of asymmetry in the molecule is the antibody-catalyzed reaction. The other three asymmetric centers are produced later by chirality transfer where only the relative stereochemistry is controlled.
-
-
-
-
13
-
-
0142085783
-
-
Anderson, J.F.; Kaya, H.K., Eds;, Academic Press: New York, Chapter 12
-
Lanier, G.N.; Silverstein, R.M.; Peacock, J.W. In Perspectives of Forest Entomology; Anderson, J.F.; Kaya, H.K., Eds;, Academic Press: New York, 1976; Chapter 12.
-
(1976)
Perspectives of Forest Entomology
-
-
Lanier, G.N.1
Silverstein, R.M.2
Peacock, J.W.3
-
14
-
-
0012335566
-
-
Lanier, G.N.; Gore, W.E.; Pearce, G.T.; Peacock, J.W.; Silverstein, R.M. J. Chem. Ecol. 1977, 3, 1.
-
(1977)
J. Chem. Ecol.
, vol.3
, pp. 1
-
-
Lanier, G.N.1
Gore, W.E.2
Pearce, G.T.3
Peacock, J.W.4
Silverstein, R.M.5
-
15
-
-
0010989620
-
-
Pearce, G.T.; Gore, W.E.; Silverstein, R.M.; Peacock, J.W.; Cuthbert, P.A.; Lanier, G.N.:;Simeone, J.B. J. Chem. Ecol. 1975, 1, 115.
-
(1975)
J. Chem. Ecol.
, vol.1
, pp. 115
-
-
Pearce, G.T.1
Gore, W.E.2
Silverstein, R.M.3
Peacock, J.W.4
Cuthbert, P.A.5
Lanier, G.N.6
Simeone, J.B.7
-
16
-
-
0016813567
-
-
(a) Gore, W.E.; Pearce, G.T.; Silverstein, R.M. J. Org. Chem. 1975, 40, 1705.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 1705
-
-
Gore, W.E.1
Pearce, G.T.2
Silverstein, R.M.3
-
17
-
-
0017311832
-
-
(b) Pearce, G.T.; Gore, W.E.; Silverstein, R.M. J. Org. Chem. 1976, 41, 2797.
-
(1976)
J. Org. Chem.
, vol.41
, pp. 2797
-
-
Pearce, G.T.1
Gore, W.E.2
Silverstein, R.M.3
-
19
-
-
0017079010
-
-
(d) Mori, K. Tetrahedron 1976, 32, 1979.
-
(1976)
Tetrahedron
, vol.32
, pp. 1979
-
-
Mori, K.1
-
26
-
-
0038581986
-
-
(k) Plaumann, D.E.; Fitzsimmons, B.J.; Ritchie, B.M.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 941.
-
(1982)
J. Org. Chem.
, vol.47
, pp. 941
-
-
Plaumann, D.E.1
Fitzsimmons, B.J.2
Ritchie, B.M.3
Fraser-Reid, B.4
-
28
-
-
0040087578
-
-
(m) Lagrange, A.; Olesker, A.: Soares Costa, S.; Lukacs, G.; Thang, T.T. Carbohydrate Res. 1982, 110, 159.
-
(1982)
Carbohydrate Res.
, vol.110
, pp. 159
-
-
Lagrange, A.1
Olesker, A.2
Soares Costa, S.3
Lukacs, G.4
Thang, T.T.5
-
32
-
-
0038903216
-
-
Elliott, W.J.; Hromnak, G.; Fried, J.; Lanier, G.N. J. Chem. Ecol. 1979, 5, 279.
-
(1979)
J. Chem. Ecol.
, vol.5
, pp. 279
-
-
Elliott, W.J.1
Hromnak, G.2
Fried, J.3
Lanier, G.N.4
-
34
-
-
0000561631
-
-
(b) Reymond, J.-L.; Jahangiri, G.K.; Stoudt, C., Lerner, R.A. J. Am. Chem. Soc. 1993, 115, 3909.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 3909
-
-
Reymond, J.-L.1
Jahangiri, G.K.2
Stoudt, C.3
Lerner, R.A.4
-
35
-
-
33748239497
-
-
Reymond, J.-E.; Janda, K.D.; Lerner, R.A. Angew. Chem., Int. Ed. Engl. 1991, 30, 17111.
-
(1991)
Angew. Chem., Int. Ed. Engl.
, vol.30
, pp. 17111
-
-
Reymond, J.-E.1
Janda, K.D.2
Lerner, R.A.3
-
36
-
-
0027136289
-
-
Sinha, S.C.; Keinan, E.; Reymond, J.-E. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11910.
-
(1993)
Proc. Natl. Acad. Sci. U.S.A.
, vol.90
, pp. 11910
-
-
Sinha, S.C.1
Keinan, E.2
Reymond, J.-E.3
-
37
-
-
0000693982
-
-
Sinha, S.C.; Keinan, E.; Reymond, J.-L. J. Am. Chem. Soc. 1993, 115, 4893.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 4893
-
-
Sinha, S.C.1
Keinan, E.2
Reymond, J.-L.3
-
38
-
-
0029639988
-
-
Shabat, D.; Itzhaky, H.; Reymond, J.-L.; Keinan, E. Nature, 1995, 374, 143.
-
(1995)
Nature
, vol.374
, pp. 143
-
-
Shabat, D.1
Itzhaky, H.2
Reymond, J.-L.3
Keinan, E.4
-
39
-
-
0038903217
-
-
note
-
Assay conditions: antibody (0.5 μM), substrate (50-500 μM), 1,3-bis[tris(hydroxymethyl) methylamino]propane-buffered saline (50 mM, pH 6.5, 50 mM NaCl). All reactions were carried out at 24 °C and monitored at 254 nm by RP-HPLC (Hitachi L-6200A equipped with a Spherisorb column (25 cm × 4.6 mm, C18, 5 μm) using 42:58 acetonitrile:water at 0.8 mL/min.
-
-
-
-
40
-
-
0038903218
-
-
note
-
In one experiment, a mixture of all four compounds, 9a-d, was subjected to antibody-catalyzed hydrolysis, resulting in complete, selective consumption of 9a with essentially no change in the concentration of 9b and small decrease of 9c,d. However, since enol ethers 9c,d are hydrolyzed approximately ten times faster than 9a,b under the same buffer conditions, in order to achieve high ee and avoid contamination of the product by racemic 5, it was necessary to remove 9b-d from the mixture before the antibody-catalyzed step.
-
-
-
-
41
-
-
33845554892
-
-
(a) Evans, D.A.; Ennis, MD.; Mathre, D.J. J. Am. Chem. Soc. 1982, 104, 1737.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 1737
-
-
Evans, D.A.1
Ennis, M.D.2
Mathre, D.J.3
-
43
-
-
0025857681
-
-
(c) Correa, A.; Denis, J.-N; Greene, A.E. Synth. Commun. 1991, 21, 1.
-
(1991)
Synth. Commun.
, vol.21
, pp. 1
-
-
Correa, A.1
Denis, J.-N.2
Greene, A.E.3
-
44
-
-
33751385567
-
-
(d) Shin, I.; Zhou, H.-Q.; Que, N.L.S.; Liu, H.-W. Swedenborg, P.D.; Jones, R.L. J. Org. Chem. 1993, 58, 2923. The absolute configuration at the homobenzylic position was assigned on the basis of the many examples reported by Evans, including a closely related asymmetric alkylation reaction with unsubstituted benzyl bromide.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 2923
-
-
Shin, I.1
Zhou, H.-Q.2
Que, N.L.S.3
Liu, H.-W.4
Swedenborg, P.D.5
Jones, R.L.6
-
45
-
-
0016756272
-
-
Antibody 14D9 is the product of a murine hybridoma cell line. It is made by producing ascites fluid from this cell line followed by ammonium sulfate precipitation, anion exchange, and affinity chromatography with immobilized G protein: (a) Köhler, G.; Milstein, C. Nature 1975, 256, 495.
-
(1975)
Nature
, vol.256
, pp. 495
-
-
Köhler, G.1
Milstein, C.2
-
47
-
-
0000893035
-
-
(a) Bednarski, M.D.; Chenault, H.K.; Simon, E.S.; Whitesides, G.M. J. Am. Chem. Soc. 1987, 109, 1283.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 1283
-
-
Bednarski, M.D.1
Chenault, H.K.2
Simon, E.S.3
Whitesides, G.M.4
-
48
-
-
0024382916
-
-
(b) Wong, C.-H. Science 1989, 244, 1145.
-
(1989)
Science
, vol.244
, pp. 1145
-
-
Wong, C.-H.1
-
49
-
-
0026418434
-
-
Trost, B.M. Science 1991, 254, 1471.
-
(1991)
Science
, vol.254
, pp. 1471
-
-
Trost, B.M.1
-
50
-
-
2542433188
-
-
Carsen, P.H.J.; Hatsuki, T.; Martin, V.S.; Sharpless, K.B. J. Org. Chem. 1981, 46, 3936.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 3936
-
-
Carsen, P.H.J.1
Hatsuki, T.2
Martin, V.S.3
Sharpless, K.B.4
-
51
-
-
0010640653
-
-
Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543.
-
(1969)
J. Org. Chem.
, vol.34
, pp. 2543
-
-
Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
-
53
-
-
0016670807
-
-
Anderson, R.J.; Corbin, V.L.; Cotterrell, G.; Cox, G.R.; Henrick, C.A.; Sehaub, F.; Siddall, J.B. J. Am. Chem. Soc. 1975, 97, 1197.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 1197
-
-
Anderson, R.J.1
Corbin, V.L.2
Cotterrell, G.3
Cox, G.R.4
Henrick, C.A.5
Sehaub, F.6
Siddall, J.B.7
-
54
-
-
0000556911
-
-
Burgess, K.; Cassidy, J.; Ohlmeyer, M.J. J. Org. Chem. 1991, 56, 1020.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 1020
-
-
Burgess, K.1
Cassidy, J.2
Ohlmeyer, M.J.3
-
55
-
-
0000221693
-
-
The closest literature precedents involve enantioselective protonation of various metal enolates. See, for example: (a) Fehr, C.; Galindo, J. J. Am. Chem. Soc. 1988, 110, 6909.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 6909
-
-
Fehr, C.1
Galindo, J.2
-
58
-
-
0001178183
-
-
and references cited therein
-
(d) Vedejs, E.; Lee, N.; Sakata, S.T. J. Am. Chem. Soc. 1994, 116, 2175 and references cited therein.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 2175
-
-
Vedejs, E.1
Lee, N.2
Sakata, S.T.3
|