Synthesis of sulfur-containing glycerophospholipids

Journal of Sulfur Chemistry

Volumn 28, Issue 1, 2007, Pages 45-72

  Davy, Jason A ^a   Wang, Zhongyi ^a   Notter, Robert H ^b   Schwan, Adrian L ^a  

^a UNIVERSITY OF GUELPH   (Canada)

^b UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

Author keywords

Biological activity; Lipases; Lipid analogs; Phospholipids; Phosphonolipids; Sulfur; Synthesis

Indexed keywords

BIOACTIVITY; LIPASES; PHOSPHOLIPIDS;

GLYCEROPHOSPHOLIPIDS; LIPID ANALOG; MEDICINAL CHEMISTRY; NATURAL SUBSTRATES; PHOSPHONOLIPID; SULPHUR ATOMS; SYNTHETIC ORGANIC CHEMISTRY;

SULFUR;

EID: 33947315272     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990601080166     Document Type: Review

References (139)

1. W.W. Christie. Lipid Technology, 15, 105 (2003).
2. S.L. Morris-Natschke, K.S. Ishaq, L.S. Kucera. Curr. Pharm. Des., 9, 1441 (2003).
3. T. Dewa, S.L. Regen. J. Am. Chem. Soc., 118, 7069 (1996).
4. D.L. Scott, S.P. White, Z. Otwinowski, W. Yuan, M. Gelb, P.B. Sigler. Science, 250, 1541 (1990).
5. D.A. Tyrrell, T.D. Heath, C.M. Colley, B.E. Ryman. Biochim. Biophys Acta, 457, 259 (1976).
6. A.A. Farooqui, L.A. Horrocks. Oily Press Lipid Library, 17, 107 (2004).
7. L. Kalvodova, N. Kahya, P. Schwille, R. Ehehalt, P. Verkade, D. Drechsel, K. Simons. J. Biol. Chem., 280, 36815 (2005).
8. H. Su, G. McClarty, F. Dong, G.M. Hatch, Z.K. Pan, G. Zhong. J. Biol. Chem., 279, 9409 (2004).
9. X.-L. Sun, W. Cui, T. Kai, E.L. Chaikof. Tetrahedron, 60, 11765 (2004).
10. L. Vares, A.V. Koulov, B.D. Smith. J. Org. Chem., 68, 10073 (2003).
11. M.-L. Alcaraz, L. Peng, P. Klotz, M. Goeldner. J. Org. Chem., 61, 192 (1996).
12. G.S. Hird, T.J. McIntosh, A.A. Ribeiro, M.W. Grinstaff. J. Am. Chem. Soc., 124, 5983 (2002).
13. Y.-A. Kim, H.-M. Chung, J.-S. Park, W. Choi, J. Min, N.-H. Park, K.-H. Kim, G.-J. Jhon, S.-Y. Han. J. Org. Chem., 68, 10162 (2003).
14. H. Tamamura, B. Bienfait, K. Nacro, N.E. Lewin, P.M. Blumberg, V.E. Marquez. J. Med. Chem., 43, 3209 (2000).
15. Y. Chang, Z. Wang, R.H. Notter, Z. Wang, L. Qu, A.L. Schwan. Bioorg. Med. Chem. Lett., 14, 5983 (2004).
16. M. Murata, H. Uchida, K. Achiwa. Chem. Pharm. Bull., 40, 2849 (1992).
17. F. Paltauf, A. Hermetter. Prog. Lipid Res., 33, 239 (1994).
18. J. Hajdu. Recent Research Developments in Lipids, 3, 165 (1999).
19. R. Gigg. Chem. Phys. Lipids, 26, 287 (1980).
20. H. Eibl. Chem. Phys. Lipids, 26, 405 (1980).
21. R. Bittman. In Lipid Synthesis and Manufacture, F.D. Gunstone (Ed.), p. 185, CRC Press, Boca Raton (1999).
22. R. Bittman. In Phospholipids Handbook, G. Cevc (Ed.), p. 141, Marcel Dekker, Inc., NewYork (1993).
23. H. Van Den Bosch, A.W.M. Zomer, W.J. Gelsema, R.J.A. Wanders, R.B.H. Schutgens. Verhandelingen - Koninklijke Nederlandse Akademie vanWetenschappen, Afdeling Natuurkunde, Tweede Reeks, 95, 75 (1995).
24. We adopt the more formal 'thiolester' rather than 'thioester' clarifying that the sulfur is not part of the carbonyl group. The 'sn-#' practice is generally accepted for indicating the positional attachment and stereochemistry of groups on a glycerol backbone. See H. Hirschmann. J. Biol. Chem. 235, 2762 (1960)
25. and IUPAC-IUB Commission on Biochemical Nomenclature (CBN). Eur. J. Biochem. 2, 127 (1967).
26. S. Morris-Natschke, J.R. Surles, L.W. Daniel, M.E. Berens, E.J. Modest, C. Piantadosi. J. Med. Chem., 29, 2114 (1986).
27. W.E. Berdel, M. Fromm, U. Fink, W. Pahlke, U. Bicker, A. Reichert, J. Rastetter. Cancer Res., 43, 5538 (1983).
28. C.I. Hong, A. Nechaev, A.J. Kirisits, R. Vig, C.R.West, K.K. Manouilov, C.K. Chu. J. Med. Chem., 39, 1771 (1996).
29. L.S. Kucera, S.L. Morris-Natschke, K.S. Ishaq, J. Hes, N. Iyer, P.A. Furman, R.A. Fleming. Nucleosides, Nucleotides, 23, 385 (2004).
30. G.M.T. VanWijk, K.Y. Hostetler, H. Van den Bosch. J. Lipid Res., 33, 1211 (1992).
31. K.L. Meyer, C.J. Marasco, Jr., S.L. Morris-Natschke, K.S. Ishaq, C. Piantadosi, L.S. Kucera. J. Med. Chem., 34, 1377 (1991).
32. A. Wissner, P.E. Sum, R.E. Schaub, C.A. Kohler, B.M. Goldstein. J. Med. Chem., 27, 1174 (1984).
33. P. G. Munder, M. Modolell, W. Bausert, H. F. Oettgen, O.Westphal. Prog. Cancer Res. Ther., 16, 441 (1981).
34. M. Nali, B. Rindone, E. Bosone, P. Farina, S. Innocenti, U. Valcavi. Gazz. Chim. Ital., 116, 25 (1986).
35. D.D. Lawson, H.R. Getz, D.A. Miller. J. Org. Chem., 26, 615 (1961).
36. A. Hermetter, F. Paltauf. Chem. Phys. Lipids, 28, 111 (1981).
37. B.M. Trost, D.P. Curran. Tetrahedron Letters, 22, 1287 (1981).
38. T. Mavromoustakos, E. Theodoropoulou, D.P.Yang, S.Y. Lin, M. Koufaki, A. Makriyannis. Chem. Phys. Lipids, 84, 21 (1996).
39. S.K. Bhatia, J. Hajdu. J. Org. Chem., 53, 5034 (1988).
40. O.P. Kuipers, N. Dekker, H.M. Verheij, G.H. de Haas. Biochemistry, 29, 6094 (1990).
41. S.L. Morris-Natschke, F. Gumus, C.J. Marasco, Jr., K.L. Meyer, M. Marx, C. Piantadosi, M.D. Layne, E.J. Modest. J. Med. Chem., 36, 2018 (1993).
42. C. Piantadosi, K.S. Ishaq, R.L.Wykle, F. Snyder. Biochemistry, 10, 1417 (1971).
43. W.E. Berdel, S. Danhauser, H.D. Schick, C.I. Hong, C.R.West, M. Fromm, U. Fink, A. Reichert, J. Rastetter. Lipids, 22, 943 (1987).
44. C.I. Hong, A.J. Kirisits, A. Nechaev, D.J. Buchheit, C.R.West. J. Med. Chem., 33, 1380 (1990).
45. E.J. Corey, A. Venkateswarlu. J. Am. Chem. Soc., 94, 6190 (1972).
46. C.I. Hong, S.H. An, D.J. Buchheit, A. Nechaev, A.J. Kirisits, C.R. West, W.E. Berdel. J. Med. Chem., 29, 2038 (1986).
47. M. MacCoss, E.K. Ryu, T. Matsushita. Biochem. Biophys. Res. Commun., 85, 714 (1978).
48. J.G. Moffatt, H.G. Khorana. J. Am. Chem. Soc., 83, 649 (1961).
49. C.I. Hong, A. Nechaev, A.J. Kirisits, R. Vig, C.R. West. J. Med. Chem., 36, 1785 (1993).
50. C.I. Hong, A.J. Kirisits, D.J. Buchheit, A. Nechaev, C.R. West. Canc. Drug Del., 3, 101 (1986).
51. R.L. Alexander, S.L. Morris-Natschke, K.S. Ishaq, R.A. Fleming, G.L. Kucera. J. Med. Chem., 46, 4205 (2003).
52. C. Piantadosi, C.J. Marasco, Jr., S.L. Morris-Natschke, K.L. Meyer, F. Gumus, J.R. Surles, K.S. Ishaq, L.S. Kucera, N. Iyer, C.A. Wallen, S. Piantadosi, E.J. Modest. J. Med. Chem., 34, 1408 (1991).
53. L.S. Kucera, N. Iyer, S.L. Morris-Natschke, S.Y. Chen, F. Gumus, K. Ishaq, D.B.J. Herrmann. Antiviral Chem. Chemother., 9, 157 (1998).
54. G.L. Kucera, C.L. Goff, N. Iyer, S. Morris-Natschke, K.S. Ishaq, S.D. Wyrick, R.A. Fleming, L.S. Kucera. Antiviral Res., 50, 129 (2001).
55. Z. Wang, A.L. Schwan, L.L. Lairson, J.S. O'Donnell, G.F. Byrne, A. Foye, B.A. Holm, R.H. Notter. Am. J. Physiol., 285, L550 (2003).
56. Y. Chang, Z.Wang, A.L. Schwan, Z.Wang, B.A. Holm, J.E. Baatz, R.H. Notter. Chem. Phys. Lipids, 137, 77 (2005).
57. R.H. Notter. Lung Surfactants: Basic Science and Clinical Applications, Marcel Dekker, Inc., New York (2000).
58. J.G. Turcotte, W.H. Lin, P.E. Pivarnik, A.M. Sacco, S.S. Shirali, M.M. Bermel, Z. Lu, R.H. Notter. Biochim. Biophys. Acta, 1084, 1 (1991).
59. J.G. Turcotte, A.M. Sacco, J.M. Steim, S.A. Tabak, R.H. Notter. Biochim. Biophys. Acta, 488, 235 (1977).
60. V. Skita, D.W. Chester, C.J. Oliver, J.G. Turcotte, R.H. Notter. J. Lipid Res., 36, 1116 (1995).
61. H. Liu, R.Z. Lu, J.G. Turcotte, R.H. Notter. J. Colloid Interface Sci., 167, 378 (1994).
62. H. Liu, J.G. Turcotte, R.H. Notter. J. Colloid Interface Sci., 167, 391 (1994).
63. R.A.W. Johnstone, M.E. Rose. Tetrahedron, 35, 2169 (1979).
64. S.K. Bhatia, J. Hajdu. Tetrahedron Lett., 29, 31 (1988).
65. S.K. Bhatia, J. Hajdu. Lipids, 26, 1424 (1991).
66. L. Yu, R.A. Deems, J. Hajdu, E.A. Dennis. J. Biol. Chem., 265, 2657 (1990).
67. A.F. Rosenthal. Meth. Enzymol., 35, 429 (1975).
68. L. Yu, E.A. Dennis. J. Am. Chem. Soc., 114, 8757 (1992).
69. F.F. Davidson, J. Hajdu, E.A. Dennis. Biochem. Biophys. Res. Commun., 137, 587 (1986).
70. B. Garrigues, G. Bertrand, J.P. Maffrand. Synthesis, 870 (1984).
71. S.K. Bhatia, J. Hajdu. Tetrahedron Lett., 28, 271 (1987).
72. L. Yu, E.A. Dennis. Biochemistry, 32, 10185 (1993).
73. H. Eibl. Chem. and Phys. Lipids, 28, 1 (1981).
74. J.R. Beadle, G.D. Kini, K.A. Aldern, M.F. Gardner, K.N. Wright, D.D. Richman, K.Y. Hostetler. Antiviral Chem. Chemother., 9, 33 (1998).
75. H.-S. Byun, R. Bittman. J. Org. Chem., 59, 668 (1994).
76. H.S. Hendrickson, E.K. Hendrickson. Chem. Phys. Lipids, 53, 115 (1990).
77. H.K. Lin, M.H. Gelb. J. Am. Chem. Soc., 115, 3932 (1993).
78. R. Bittman, H.S. Byun, B. Mercier, H. Salari. J. Med. Chem., 37, 425 (1994).
79. A.J. Aarsman, L.L.M. Van Deenen, H. Van den Bosch. Bioorg. Chem., 5, 241 (1976).
80. J.P. Ward. Chem. Phys. Lipids, 47, 217 (1988).
81. G.L. Kucera, C. Miller, P.J. Sisson, R.W. Wilcox, Z. Wiemer, M. Waite. J. Biol. Chem., 263, 12964 (1988).
82. M. Iwai, Y. Tsujisaka, J. Fukumoto. J. Gen. Appl. Microbiol., 10, 257 (1964).
83. J.W. Cox, L.A. Horrocks. J. Lipid Res., 22, 496 (1981).
84. S.K. Bhatia, J. Hajdu. Synthesis, 16 (1989).
85. S.K. Bhatia, J. Hajdu. Tetrahedron Lett., 28, 1729 (1987).
86. W.R. Vogler, A.C. Olson, J. Hajdu, M. Shoji, R. Raynor, J.F. Kuo. Lipids, 28, 511 (1993).
87. Y. Letourneux, J. Bourass, P. Boucrot, L. Elkihel, J.Y. Petit. Pharm. Res., 35, 73 (1997).
88. W.J. Baumann, H.K. Mangold. J. Org. Chem., 31, 498 (1966).
89. A.J. Aarsman, C.F.P. Roosenboom, G.A. Van der Marel, B. Shadid, J.H. Van Boom, H. Van den Bosch. Chem. Phys. Lipids, 36, 229 (1985).
90. L.J. Reynolds, L.L. Hughes, L. Yu, E.A. Dennis. Anal. Biochem., 217, 25 (1994).
91. C.A.A. Van Boeckel, G.A. Van der Marel, P.Westerduin, J.H. Van Boom. Synthesis, 399 (1982).
92. T.N. Wheeler, S.G. Blanchard, R.C. Andrew, F. Fang, Y. Gray-Nunez, C.O. Harris, M.H. Lambert, M.M. Mehrotra, D.J. Parks, J.A. Ray, T.L. Smalley, Jr. et al. J. Med. Chem., 37, 4118 (1994).
93. E.A. Dennis, E.J. Ackermann, R.A. Deems, L.J. Reynolds. Adv. Prostag., Thromb. L., 23, 75 (1995).
94. J.Y. Channon, C.C. Leslie. J. Biol. Chem., 265, 5409 (1990).
95. M. Fuji, F.Watanabe, Y. Fujii, H. Hashizume, T. Okuno, K. Shirahase, I. Teshirogi, M. Ohtani. J. Org. Chem., 62, 6804 (1997).
96. S.K. Bhatia, J. Hajdu. Tetrahedron Lett., 28, 3767 (1987).
97. C. Balet, K.A. Clingman, J. Hajdu. Biochem. Biophys. Res. Commun., 150, 561 (1988).
98. L. Yu, E.A. Dennis. Bioorg. Med. Chem. Lett., 2, 1343 (1992).
99. M.K. Jain, B.Z. Yu, J. Rogers, M.H. Gelb, M.D. Tsai, E.K. Hendrickson, H.S. Hendrickson. Biochemistry, 31, 7841 (1992).
100. H.S. Hendrickson, E.A. Dennis. J. Biol. Chem., 259, 5734 (1984).
101. H.S. Hendrickson, E.A. Dennis. J. Biol. Chem., 259, 5740 (1984).
102. W. Yuan, D.M. Quinn, P.B. Sigler, M.H. Gelb. Biochemistry, 29, 6082 (1990).
103. H.S. Hendrickson, E.J. Dumdei, A.G. Batchelder, G.L. Carlson. Biochemistry, 26, 3697 (1987).
104. I. Travnicek, S. Rodoni, M. Schellenberg, P. Matile. J. Plant Physiol., 155, 220 (1999).
105. J.J. Volwerk, A.G.R. Dedieu, H.M. Verheij, R. Dijkman, G.H. De Haas. Rec. Trav. Chim. Pays-Bas, 98, 214 (1979).
106. M. Shinomiya, D.E. Epps, R.L. Jackson. Biochim Biophys. Acta, 795, 212 (1984).
107. H.S. Hendrickson, E.K. Hendrickson, R.H. Dybvig. J. Lipid Res., 24, 1532 (1983).
108. L. Yu, E.A. Dennis. Meth. Enzymol., 197, 65 (1991).
109. S.Y. Okada, R. Jelinek, D. Charych. Angew. Chem., Int. Ed., 38, 655 (1999).
110. H. Eibl, S. Kovatchev. Meth. Enzymol., 72, 632 (1981).
111. F.G. Prendergast, M. Meyer, G.L. Carlson, S. Iida, J.D. Potter. J. Biol. Chem., 258, 7541 (1983).
112. W.R. Snyder. J. Lipid Res., 28, 949 (1987).
113. J.W. Cox, W.R. Snyder, L.A. Horrocks. Chem. Phys. Lipids, 25, 369 (1979).
114. C. Mihai, J. Mataka, S. Riddle, M.-D. Tsai, K.S. Bruzik. Bioorg. Med. Chem. Lett., 7, 1235 (1997).
115. H.S. Hendrickson. Biochim. Biophys. Acta, 1392, 16 (1998).
116. H.S. Hendrickson, C. Banovetz, M.J. Kirsch, E.K. Hendrickson. Chem. Phys. Lipids, 84, 87 (1996).
117. M.A. Alisi, M. Brufani, L. Filocamo, G. Gostoli, S. Maiorana, M.C. Cesta, E. Ferrari, S. Lappa, P. Pagella. Tetrahedron Lett., 33, 7793 (1992).
118. S.F. Martin, J.A. Josey, Y.-L.Wong, D.W. Dean. J. Org. Chem., 59, 4805 (1994).
119. M.A. Alisi, M. Brufani, L. Filocamo, G. Gostoli, S. Lappa, S. Maiorana, M.C. Cesta, E. Ferrari, P.G. Pagella. Tetrahedron Lett., 33, 3891 (1992).
120. L. Moroder, H.J. Musiol, G. Siglmueller. Synthesis, 889 (1990).
121. E. Wuensch, L. Moroder, S. Romani. H.-S. Z. Physiol. Chem., 363, 1461 (1982).
122. B. Mlotkowska, A. Markowska. Liebigs Ann. Chem., 923 (1990).
123. B. Mlotkowska, A. Markowska. Liebigs Ann. Chem., 833 (1991).
124. B. Mlotkowska, A. Markowska. Liebigs Ann. Chem., 1 (1984).
125. B. Mlotkowska. Liebigs Ann. Chem., 1361 (1991).
126. B. Mlotkowska, A. Markowska. Liebigs Ann. Chem., 191 (1988).
127. B. Mlotkowska, J. Olejnik. Liebigs Ann., 1467 (1995).
128. K.H. Buechel, A. Conte. Chem. Ber., 100, 1248 (1967).
129. E.K. Hendrickson, J.L. Johnson, H.S. Hendrickson. Bioorg. Med. Chem. Lett., 1, 615 (1991).
130. A.S. Bushnev, E.K. Hendrickson, V.I. Shvets, H.S. Hendrickson. Bioorg. Med. Chem., 2, 147 (1994).
131. H.S. Hendrickson, A.N. Giles, S.E. Vos. Chem. Phys. Lipids, 89, 45 (1997).
132. H.S. Hendrickson, E.K. Hendrickson. Bioorg. Med. Chem. Lett., 8, 1057 (1998).
133. G. Angelini, A. Margonelli, P. Ragni, C. Sparapani, L. Cellai, M.A. Iannelli, M.C. Cesta, S. Lappa. J. Label. Compd. Radiopharm., 39, 747 (1997).
134. R.N.A.H. Lewis, R.N. McElhaney, D.A. Mannock. CA Patent #2262071.
135. S. Ghosh, K.R.K. Easwaran, S. Bhattacharya. Tetrahedron Lett., 37, 5769 (1996).
136. R. Rosseto, N. Bibak, J. Hajdu. Org. Biomol. Chem., 4, 2358 (2006).
137. P.N. Guivisdalsky, R. Bittman, Z. Smith, M.L. Blank, F. Snyder, S. Howard, H. Salari. J. Med. Chem., 33, 2614 (1990).
138. C. Duschl, M. Liley, H. Lang, A. Ghandi, S.M. Zakeeruddin, H. Stahlberg, J. Dubochet, A. Nemetz, W. Knoll, H. Vogel. Mater. Sci. Eng., C, C4, 7 (1996).
139. N. Boden, R.J. Bushby, Q. Liu, S.D. Evans, A.T.A. Jenkins, P.F. Knowles, R.E. Miles. Tetrahedron, 54, 11537 (1998).