Nucleolipids: Natural Occurrence, Synthesis, Molecular Recognition, and Supramolecular Assemblies as Potential Precursors of Life and Bioorganic Materials

Wiley - Tập 2 Số 8 - Trang 977-1063 - 2005
Helmut Rosemeyer1
1Katholieke Universiteit Leuven, Dept. Farmaceutische Wetenschappen, Afd. Medicinale Chemie, Minderbroederstraat 10, B-3000 Leuven. [email protected]

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Ichinose, 2003, Oyo Butsuri, 72, 304

Ichinose, 2002, Chem. Rec., 2, 339, 10.1002/tcr.10032

Ichinose, 2004, Chemistry Lett., 33, 656, 10.1246/cl.2004.656

Kunitake, 2003, Jiko Soshikika ni yoru Nano Materiaru no Sosei to Oyo, 1

Smrt, 1980, Collect. Czech. Chem. Commun., 45, 927, 10.1135/cccc19800927

L. Stryer, ‘Biochemie’, F. Vieweg & Sohn, Braunschweig, 1979, p. 318.

Takatsuki, 1971, J. Antibiot., 24, 215, 10.7164/antibiotics.24.215

Tunicamycins, G. Tamura, Ed.; Japan Scientific Press, Tokyo, Japan, 1982.

Tamura, 1976, Agric. Biol. Chem., 40, 447, 10.1271/bbb1961.40.447

‘Nucleosides as Biological Probes’, John Wiley & Sons, New York 1979, pp. 4-19.

Isono, 1985, J. Antibiot., 38, 1617, 10.7164/antibiotics.38.1617

Kimura, 1998, J. Antibiot., 51, 640, 10.7164/antibiotics.51.640

Kimura, 1998, J. Antibiot., 51, 647, 10.7164/antibiotics.51.647

Ubukata, 1988, J. Am. Chem. Soc., 110, 4416, 10.1021/ja00221a052

Ubukata, 1992, J. Org. Chem., 57, 6392, 10.1021/jo00050a009

Kim, 1997, Bull. Korean Chem. Soc., 18, 465

Kim, 1995, J. Chem. Soc., Perkin Trans. 1, 1783, 10.1039/p19950001783

Kim, 1994, Bull. Korean Chem. Soc., 15, 829

Kim, 1995, J. Carbohydr. Chem., 14, 439, 10.1080/07328309508002083

Rosemeyer, 2004, Chem. Biodiv., 1, 361, 10.1002/cbdv.200490033

Acton, 1977, J. Med. Chem., 20, 1362, 10.1021/jm00221a002

Nakamura, 1984, Tetrahedron Lett., 25, 2989, 10.1016/S0040-4039(01)81345-9

Wu, 1984, Tetrahedron Lett., 25, 3719, 10.1016/0040-4039(84)80114-8

Capon, 1984, J. Am. Chem. Soc., 106, 1819, 10.1021/ja00318a045

Wu, 1986, Bull. Chem. Soc. Jpn., 59, 2495, 10.1246/bcsj.59.2495

Ishida, 1992, Chem. Pharm. Bull., 40, 766, 10.1248/cpb.40.766

Hattori, 1997, J. Nat. Prod., 60, 411, 10.1021/np960745b

Fu, 1998, J. Nat. Prod., 61, 548, 10.1021/np970454i

Mangalindan, 2000, Planta Med., 66, 364, 10.1055/s-2000-8554

Paulus, 1960, J. Biol. Chem., 235, 1303, 10.1016/S0021-9258(18)69403-7

Agranoff, 1958, J. Biol. Chem., 233, 1077, 10.1016/S0021-9258(19)77342-6

Neil, 1970, Cancer Res., 30, 1047

MacCoss, 1978, Biochem. Biophys. Res. Commun., 85, 714, 10.1016/0006-291X(78)91220-2

Matsushita, 1981, Cancer Res., 41, 2707

Ryu, 1982, J. Med. Chem., 25, 1322, 10.1021/jm00353a010

MacCoss, 1978, Biochem. Biophys. Res. Commun., 85, 714, 10.1016/0006-291X(78)91220-2

Turcotte, 1980, Biochim. Biophys. Acta, 619, 619, 10.1016/0005-2760(80)90111-3

Turcotte, 1980, Biochim. Biophys. Acta, 619, 604, 10.1016/0005-2760(80)90110-1

Hong, 1985, J. Med. Chem., 28, 171, 10.1021/jm00380a004

Wijk, 1991, Biochim. Biophys. Acta, 1084, 307, 10.1016/0005-2760(91)90074-R

Tanaka, 2000, Microbiology, 146, 377, 10.1099/00221287-146-2-377

Rosemeyer, 1985, Angew. Chem., Int. Ed., 24, 501, 10.1002/anie.198505011

Welch, 1985, Acta Chem. Scand. B, 39, 47, 10.3891/acta.chem.scand.39b-0047

Rubas, 1986, Int. J. Cancer, 37, 149, 10.1002/ijc.2910370123

Schwendener, 1985, Biochem. Biophys. Res. Commun., 126, 660, 10.1016/0006-291X(85)90235-9

Neumann, 1989, J. Am. Chem. Soc., 111, 4270, 10.1021/ja00194a018

Debouzy, 1990, Biochem. Pharmacol., 39, 1657, 10.1016/0006-2952(90)90108-W

Ahlers, 1990, Colloid Polym. Sci., 268, 132, 10.1007/BF01513191

Yun, 2003, Chem. Commun., 254, 10.1039/b210822d

Sigmund, 1996, Helv. Chim. Acta, 79, 426, 10.1002/hlca.19960790210

Howe, 1951, J. Chem. Soc., 2663, 10.1039/jr9510002663

, in ‘Ether Lipids. Biochemical and Biomedical Aspects’, Academic Press, New York, 1983, p. 389.

Wasner, 1996, Helv. Chim. Acta, 79, 609, 10.1002/hlca.19960790304

Wasner, 1996, Helv. Chim. Acta, 79, 619, 10.1002/hlca.19960790305

Moreau, 2004, J. Am. Chem. Soc., 126, 7533, 10.1021/ja039597j

Moreau, 2005, Tetrahedron Lett., 46, 1593, 10.1016/j.tetlet.2005.01.095

Iwaura, 2002, Chem. Mater., 14, 3047, 10.1021/cm020263n

Iwaura, 2003, Angew. Chem., 115, 1039, 10.1002/ange.200390232

Shimizu, 2001, J. Am. Chem. Soc., 123, 5947, 10.1021/ja010201i

Shuto, 1987, Tetrahedron Lett., 28, 199, 10.1016/S0040-4039(00)95685-5

Shuto, 1988, Chem. Pharm. Bull., 36, 209, 10.1248/cpb.36.209

Shuto, 1988, Chem. Pharm. Bull., 36, 5020, 10.1248/cpb.36.5020

Zandomeneghi, 2001, Helv. Chim. Acta, 84, 3710, 10.1002/1522-2675(20011219)84:12<3710::AID-HLCA3710>3.0.CO;2-7

Berti, 2000, Colloids Surf., A, 167, 95, 10.1016/S0927-7757(99)00466-5

Nakamura, 1998, Thin Solid Films, 327-329, 603, 10.1016/S0040-6090(98)00722-6

Li., 2001, Langmuir, 17, 2228, 10.1021/la001105i

Araki, 2001, Chem. Commun., 1826, 10.1039/b103864h

Ramirez, 1982, J. Am. Chem. Soc., 104, 5483, 10.1021/ja00384a039

Shea, 1990, Nucleic Acids Res., 18, 3777, 10.1093/nar/18.13.3777

Manoharan, 1997, Nucleosides Nucleotides, 16, 1141, 10.1080/07328319708006149

Manoharan, 1997, Nucleosides Nucleotides, 16, 1129, 10.1080/07328319708006147

Boutorine, 1993, Biochimie, 75, 35, 10.1016/0300-9084(93)90022-K

Boutorine, 1989, FEBS Lett., 254, 129, 10.1016/0014-5793(89)81023-3

Vu, 1993, Nucleosides Nucleotides, 12, 853, 10.1080/07328319308018556

Krieg, 1993, Proc. Natl. Acad. Sci. U.S.A., 90, 1048, 10.1073/pnas.90.3.1048

Rump, 1998, Bioconjugate Chem., 9, 341, 10.1021/bc970176z

Gosse, 2004, J. Phys. Chem., 108, 6485, 10.1021/jp031188m

Boutorine, 1994, Angew. Chem., 106, 2526, 10.1002/ange.19941062314

Cassell, 1998, Angew. Chem., 110, 1670, 10.1002/(SICI)1521-3757(19980605)110:11<1670::AID-ANGE1670>3.0.CO;2-8

Ötvös, 1999, Nucleosides Nucleotides, 18, 1929, 10.1080/07328319908044854

Ramzaeva, 1997, Helv. Chim. Acta, 80, 1809, 10.1002/hlca.19970800605

Seela, 1999, Helv. Chim. Acta, 82, 1878, 10.1002/(SICI)1522-2675(19991110)82:11<1878::AID-HLCA1878>3.0.CO;2-W

, , , , , , ‘High Density Labeling of DNA with Modified or ‘Chromophore’ Carrying Nucleotides and DNA Polymerases Used', PCT Application WO 00/68422, 16. 11. 2000.

Kim, 2004, ChemBioChem, 5, 1517, 10.1002/cbic.200400150

Kim, 2003, Nucleic Acids Res., 31, 2725, 10.1093/nar/gkg391

‘Supramolecular Chemistry’, VCH, Weinheim, 1995.

Ariga, 1998, Acc. Chem. Res., 31, 371, 10.1021/ar970014i

‘Principles of Nucleic Acid Structure’, Springer Verlag, Berlin, 1984.

Ahlers, 1990, Angew. Chem., 102, 1310, 10.1002/ange.19901021114

Kitano, 1985, Bull. Chem. Soc. Jpn., 58, 2826, 10.1246/bcsj.58.2826

Weck, 1997, Langmuir, 13, 3515, 10.1021/la970095r

Tsiourvas, 1996, J. Phys. Chem., 100, 14087, 10.1021/jp9603344

Paleos, 1997, Adv. Mater., 9, 695, 10.1002/adma.19970090904

Rädler, 1998, Langmuir, 14, 6620, 10.1021/la980515s

Shimomura, 1997, J. Am. Chem. Soc., 119, 2341, 10.1021/ja962847u

Huang, 1997, Synth. Commun., 27, 681, 10.1080/00397919708003342

Huang, 1997, Spectrosc. Lett., 30, 1441, 10.1080/00387019708006736

Huang, 1998, Thin Solid Films, 325, 210, 10.1016/S0040-6090(98)00489-1

Huang, 1998, Thin Solid Films, 326, 217, 10.1016/S0040-6090(98)00527-6

Li, 2000, Langmuir, 16, 7701, 10.1021/la000181i

Huang, 2000, Langmuir, 16, 3937, 10.1021/la990947i

Li, 2001, Langmuir, 17, 2228, 10.1021/la001105i

Li, 2001, Spectrochim. Acta, Part A, 57, 1587, 10.1016/S1386-1425(01)00392-4

Miao, 2003, Spectrochim. Acta, Part A, 59, 1045, 10.1016/S1386-1425(02)00292-5

Miao, 2003, Langmuir, 19, 5389, 10.1021/la0345690

Kawahara, 1992, Chem. Lett., 1839, 10.1246/cl.1992.1839

Berti, 1997, Langmuir, 13, 3438, 10.1021/la970334a

Baglioni, 2003, Curr. Opin. Colloid Interface Sci., 8, 55, 10.1016/S1359-0294(03)00015-3

Fortini, 2004, Curr. Opin. Colloid Interface Sci., 9, 168, 10.1016/j.cocis.2004.05.025

Nowick, 1993, J. Am. Chem. Soc., 115, 7636, 10.1021/ja00070a007

Nowick, 1994, J. Am. Chem. Soc., 116, 3285, 10.1021/ja00087a014

Berti, 2000, Colloids Surf., A, 167, 95, 10.1016/S0927-7757(99)00466-5

Bombelli, 2002, J. Phys. Chem. B, 106, 11613, 10.1021/jp020463m

Bombelli, 2004, J. Phys. Chem. B, 108, 16427, 10.1021/jp047816x

Berti, 1999, J. Phys. Chem. B, 103, 4916, 10.1021/jp990504n

Berti, 1999, J. Phys. Chem. B, 103, 1738, 10.1021/jp983424c

Berti, 2000, Physica B, 276-278, 334, 10.1016/S0921-4526(99)01534-3

Berti, 1998, J. Phys. Chem. B, 102, 303, 10.1021/jp972954q

Bachmann, 1992, Nature, 357, 57, 10.1038/357057a0

Berndt, 1995, Langmuir, 11, 3083, 10.1021/la00008a038

Ebara, 1996, Langmuir, 12, 5165, 10.1021/la9603885

Itojima, 1992, Biochemistry, 31, 4757, 10.1021/bi00135a003

Gottarelli, 1995, Chem. Commun., 2555, 10.1039/c39950002555

Davis, 2004, Angew. Chem., 116, 684, 10.1002/ange.200300589

Gottarelli, 1999, Liq. Cryst., 26, 965, 10.1080/026782999204318

Gottarelli, 1998, Helv. Chim. Acta, 81, 2078, 10.1002/(SICI)1522-2675(19981111)81:11<2078::AID-HLCA2078>3.0.CO;2-7

Pieraccini, 2001, Chirality, 13, 7, 10.1002/1520-636X(2001)13:1<7::AID-CHIR3>3.0.CO;2-M

Mezzina, 2001, Chem. Eur. J., 7, 388, 10.1002/1521-3765(20010119)7:2<388::AID-CHEM388>3.0.CO;2-V

Marlow, 1999, J. Org. Chem., 64, 5116, 10.1021/jo9901440

Gottarelli, 2000, Chem. Eur. J., 6, 3242, 10.1002/1521-3765(20000901)6:17<3242::AID-CHEM3242>3.0.CO;2-K

Manet, 2001, Helv. Chim. Acta, 84, 2096, 10.1002/1522-2675(20010711)84:7<2096::AID-HLCA2096>3.0.CO;2-G

Park, 2003, Chem. Commun., 2912, 10.1039/B311249G

Snip, 2001, Tetrahedron Lett., 42, 2153, 10.1016/S0040-4039(01)00095-8

Numata, 2003, Chem. Lett., 32, 308, 10.1246/cl.2003.308

‘A Revolution in the Physiology of the Living Cell’, Krieger Publishing Company, Malabar, Florida, 1992.

Reimer, 1995, Biochemistry, 34, 12877, 10.1021/bi00039a050

Sastry, 2001, Chem. Commun., 1434, 10.1039/b101110n

Luisi, 2002, Anat. Rec., 268, 208, 10.1002/ar.10155

Andrisano, 1999, Angew. Chem., 111, 2543, 10.1002/(SICI)1521-3757(19990816)111:16<2543::AID-ANGE2543>3.0.CO;2-G

Forman, 2000, J. Am. Chem. Soc., 122, 4060, 10.1021/ja9925148

Masiero, 2000, Chem. Commun., 1995, 10.1039/b006160n

Rinaldi, 2001, Appl. Phys. Lett., 78, 3541, 10.1063/1.1374232

Rinaldi, 2000, Cond. Matter, 1