-
8
-
-
0026573465
-
-
(a) Snyder, F.; Lee, T.-C.; Blank, M. L. Prog. Lipid Res. 1992, 31, 65.
-
(1992)
Prog. Lipid Res.
, vol.31
, pp. 65
-
-
Snyder, F.1
Lee, T.-C.2
Blank, M.L.3
-
10
-
-
0026362632
-
-
(a) Bodine, P. V.; Garcia, M. L.; Pascual, J.; Bastida, E.; Carganico, G.; Litwack, G. Receptor 1991, 1, 167.
-
(1991)
Receptor
, vol.1
, pp. 167
-
-
Bodine, P.V.1
Garcia, M.L.2
Pascual, J.3
Bastida, E.4
Carganico, G.5
Litwack, G.6
-
11
-
-
0026602693
-
-
(b) Schulman, G.; Bodine, P. V.; Litwack, G. Biochemistry 1990, 31, 1734.
-
(1990)
Biochemistry
, vol.31
, pp. 1734
-
-
Schulman, G.1
Bodine, P.V.2
Litwack, G.3
-
12
-
-
0028988839
-
-
Sanson, A.; Monck, M. A.; Neumann, J.-M. Biochemistry 1995, 34, 5938.
-
(1995)
Biochemistry
, vol.34
, pp. 5938
-
-
Sanson, A.1
Monck, M.A.2
Neumann, J.-M.3
-
16
-
-
0029753778
-
-
(b) Balboa, M. A.; Balsinde, J.; Winstead, M. V.; Tischfeld, J. A.; Dennis, E. A. J. Biol. Chem. 1996, 271, 32381.
-
(1996)
J. Biol. Chem.
, vol.271
, pp. 32381
-
-
Balboa, M.A.1
Balsinde, J.2
Winstead, M.V.3
Tischfeld, J.A.4
Dennis, E.A.5
-
17
-
-
0001755721
-
-
(a) Vigmond, S. S.; Dewa, T.; Regen, S. L. J. Am. Chem. Soc. 1995, 117, 7838.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 7838
-
-
Vigmond, S.S.1
Dewa, T.2
Regen, S.L.3
-
19
-
-
0032556231
-
-
Carion-Taravella, B.; Lesieur, S.; Ollivon, M.; Chopineau, J. J. Am. Chem. Soc. 1998, 120, 10588.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 10588
-
-
Carion-Taravella, B.1
Lesieur, S.2
Ollivon, M.3
Chopineau, J.4
-
20
-
-
0028236552
-
-
Tocanne, J.-F.; Dupou-Cezanne, L.; Lopez, A. Prog. Lipid Res. 1994, 33, 203.
-
(1994)
Prog. Lipid Res.
, vol.33
, pp. 203
-
-
Tocanne, J.-F.1
Dupou-Cezanne, L.2
Lopez, A.3
-
21
-
-
0026492542
-
-
White, J. M. Science 1992, 258, 917.
-
(1992)
Science
, vol.258
, pp. 917
-
-
White, J.M.1
-
22
-
-
0004094125
-
-
Watts, A., Ed.; Elsevier: Amsterdam
-
Sandermann, H.; Duncan, T. M.; McIntyre, J. O.; Fleischer, S. In Protein-Lipid Interactions; Watts, A., Ed.; Elsevier: Amsterdam, 1993; p 67.
-
(1993)
Protein-lipid Interactions
, pp. 67
-
-
Sandermann, H.1
Duncan, T.M.2
McIntyre, J.O.3
Fleischer, S.4
-
23
-
-
0001664792
-
-
Cerc, G., Ed.; Marcel Dekker: New York
-
Bittman, R. In Phospholipid Handbook; Cerc, G., Ed.; Marcel Dekker: New York, 1993; p 141.
-
(1993)
Phospholipid Handbook
, pp. 141
-
-
Bittman, R.1
-
24
-
-
0026535462
-
-
Hebert, N.; Beck, A.; Lennox, R. B.; Just, G. J. Org. Chem. 1992, 57, 1777.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 1777
-
-
Hebert, N.1
Beck, A.2
Lennox, R.B.3
Just, G.4
-
25
-
-
0027989427
-
-
(a) Martin, S. F.; Josey, J. A.; Wong, V.-L.; Dean, D. W. J. Org. Chem. 1994, 59, 4805.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4805
-
-
Martin, S.F.1
Josey, J.A.2
Wong, V.-L.3
Dean, D.W.4
-
27
-
-
0028858245
-
-
(a) Srisiri, W.; Lee, Y.-S.; O'Brien, D. F. Tetrahedron Lett. 1995, 36, 8945.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 8945
-
-
Srisiri, W.1
Lee, Y.-S.2
O'Brien, D.F.3
-
28
-
-
0029827164
-
-
(b) Srisiri, W.; Lamparski, H. G.; O'Brien, D. F. J. Org. Chem. 1996, 61, 5911.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 5911
-
-
Srisiri, W.1
Lamparski, H.G.2
O'Brien, D.F.3
-
29
-
-
0023608120
-
-
Burgos, C. E.; Ayer, D. E.; Johnson, R. A. J. Org. Chem. 1987, 52, 4973.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 4973
-
-
Burgos, C.E.1
Ayer, D.E.2
Johnson, R.A.3
-
37
-
-
0345553984
-
-
note
-
4 could also be accomplished in high yield, substantial losses occurred on isolation of the product, most likely as a result of chelation of aluminum by the bis-diol function of compound 6.
-
-
-
-
38
-
-
0345553983
-
-
note
-
19-21 resulted in lower yields as well: compound 7b was obtained in 43% along with the sn-2-regioisomer (10%) and the 1,2-diacyl product (8.1%), compared to the 71% yield obtained under the reaction conditions shown in Scheme 1.
-
-
-
-
39
-
-
0024498774
-
-
1H NMR spectra of phosphatidylcholines and related derivatives, see: Sparling, M. L.; Zidovetzki, R.; Muller, L.; Chan, S. I. Anal. Biochem. 1989, 178, 67.
-
(1989)
Anal. Biochem.
, vol.178
, pp. 67
-
-
Sparling, M.L.1
Zidovetzki, R.2
Muller, L.3
Chan, S.I.4
-
40
-
-
0345553982
-
-
note
-
We observed no significant acyl migration during the workup and subsequent chromatography.
-
-
-
-
41
-
-
0010640653
-
-
Mosher, H. S.; Dale, J. A.; Dull, D. L. J. Org. Chem. 1969, 34, 2543.
-
(1969)
J. Org. Chem.
, vol.34
, pp. 2543
-
-
Mosher, H.S.1
Dale, J.A.2
Dull, D.L.3
-
43
-
-
0023853788
-
-
(b) Balet, C.; Clingman, K. A.; Hajdu, J. Biochem. Biophys. Res. Commun. 1988, 150, 561.
-
(1988)
Biochem. Biophys. Res. Commun.
, vol.150
, pp. 561
-
-
Balet, C.1
Clingman, K.A.2
Hajdu, J.3
-
44
-
-
0345478327
-
-
Byun, H.-S.; Erukulla, R. K.; Bittman, R. J. Org. Chem., 1994, 56, 2630.
-
(1994)
J. Org. Chem.
, vol.56
, pp. 2630
-
-
Byun, H.-S.1
Erukulla, R.K.2
Bittman, R.3
-
45
-
-
0025078714
-
-
Medeiros, E.; Herbert, J. M.; Taylor, R. J. K. Tetrahedron Lett. 1990, 31, 5843.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 5843
-
-
Medeiros, E.1
Herbert, J.M.2
Taylor, R.J.K.3
-
47
-
-
0344114246
-
-
(b) Ganong, B. R.; Loomis,; Hannun, Y. A.; Bell, R. M. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 1184.
-
(1986)
Proc. Natl. Acad. Sci. U.S.A.
, vol.83
, pp. 1184
-
-
Ganong, B.R.1
Loomis2
Hannun, Y.A.3
Bell, R.M.4
-
50
-
-
0021435455
-
-
It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
-
(1984)
Biophys. J.
, vol.45
, pp. 901
-
-
Chowdry, B.Z.1
Lipka, G.2
Dalziel, A.W.3
Sturtevant, J.M.4
-
51
-
-
0017343137
-
-
It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
-
(1977)
J. Biol. Chem.
, vol.525
, pp. 2405
-
-
Roberts, M.F.1
Deems, R.A.2
Dennis, E.A.3
-
52
-
-
0025193523
-
-
It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
-
(1990)
J. Biol. Chem.
, vol.265
, pp. 2657
-
-
Yu, L.1
Deems, R.A.2
Hajdu, J.3
Dennis, E.A.4
-
53
-
-
0025071607
-
-
It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
-
(1990)
Biochim. Biophys. Acta
, vol.1046
, pp. 249
-
-
DeHaas, G.H.1
Dijkman, R.2
Ransac, S.3
Verger, R.4
-
54
-
-
0021341815
-
-
It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
-
(1984)
Blood
, vol.63
, pp. 545
-
-
Hoffman, D.R.1
Hajdu, J.2
Snyder, F.3
-
55
-
-
0027763550
-
-
It has been well documented that both naturally occurring and synthetic phospholipids show significant changes in response to variation of the polar phosphoester substituent in thermotropic properties (cf. Chowdry, B. Z.; Lipka, G.; Dalziel, A. W.; Sturtevant, J. M. Biophys. J. 1984, 45, 901) enzyme-substrate behavior (Roberts, M. F.; Deems, R. A.; Dennis, E. A. J. Biol. Chem. 1977, 525, 2405), inhibitory potency (Yu, L.; Deems, R. A.; Hajdu, J.; Dennis, E. A. J. Biol. Chem. 1990, 265, 2657. DeHaas, G. H.; Dijkman, R.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1990, 1046, 249), and antitumor activity (Hoffman, D. R.; Hajdu, J.; Snyder, F. Blood 1984, 63, 545). For a recent application of headgroup-modified phospholipids in the design of new drug delivery systems, see: Wang, P.; Schuster, M.; Wang, Y.-F.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 10487.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 10487
-
-
Wang, P.1
Schuster, M.2
Wang, Y.-F.3
Wong, C.-H.4
-
56
-
-
0028075333
-
-
Slater, S. J.; Kelly, M. B.; Taddeo, F. J.; Ho, C.; Rubin, E.; Stubbs, C. D. J. Biol. Chem. 1994, 269, 4866.
-
(1994)
J. Biol. Chem.
, vol.269
, pp. 4866
-
-
Slater, S.J.1
Kelly, M.B.2
Taddeo, F.J.3
Ho, C.4
Rubin, E.5
Stubbs, C.D.6
-
58
-
-
0025027265
-
-
Thunnissen, M. M. G. M.; Ab, E.; Kalk, K. H.; Drenth, J.; Dijkstra, B. W.; Kuipers, O. P.; Dijkman, R.; de Haas, G. H.; Verheij, H. M. Nature 1990, 347, 689.
-
(1990)
Nature
, vol.347
, pp. 689
-
-
Thunnissen, M.M.G.M.1
Ab, E.2
Kalk, K.H.3
Drenth, J.4
Dijkstra, B.W.5
Kuipers, O.P.6
Dijkman, R.7
De Haas, G.H.8
Verheij, H.M.9
-
61
-
-
0001846306
-
-
Cevc, G., Ed.; Marcel Dekker: New York
-
(b) Cevc, G.; Seddon, J. M. In Phospholipid Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 351-401.
-
(1993)
Phospholipid Handbook
, pp. 351-401
-
-
Cevc, G.1
Seddon, J.M.2
-
64
-
-
0029892370
-
-
Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1573
-
-
Janout, V.1
Lanier, M.2
Regen, S.L.3
-
66
-
-
0344260113
-
-
note
-
(b) The absorption spectrum of the dansyl chromophore overlaps with the emission spectra of β-naphthylacetyl group. The N-methylanthranoyl fluorophore also absorbs at the emission maximum of the β-naphthylacetyl sprctrum (see the Experimental Section).
-
-
-
-
68
-
-
0344691858
-
-
personal communication
-
(b) Bales, B. L., personal communication.
-
-
-
Bales, B.L.1
-
69
-
-
37049075132
-
-
Nitroxide spin labels are known to be unstable under acidic conditions; see: Cardellini, L.; Carloni, P.; Damian, E.; Greci, L.; Stipa, P.; Rizzoli, C.; Sgarabatto, P. J. Chem Soc., Perkin Trans. 2 1994, 769.
-
(1994)
J. Chem Soc., Perkin Trans. 2
, pp. 769
-
-
Cardellini, L.1
Carloni, P.2
Damian, E.3
Greci, L.4
Stipa, P.5
Rizzoli, C.6
Sgarabatto, P.7
-
72
-
-
0344691856
-
-
note
-
The p-nitrophenyl eater of 12-TCBOC-aminolauric acid was prepared in reaction between 12-TCBOC-aminolauric acid and p-nitrophenol using DCC as coupling agent.
-
-
-
|