Synthesis of oligosaccharide-polylysine conjugates: A well characterized sialyl Lewisa polymer for ELISA

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7414-7415

  Thoma, Gebhard ^a   Magnani, John L ^b   Öhrlein, Reinhold ^a   Ernst, Beat ^a   Schwarzenbach, Franz ^a   Duthaler, Rudolf O ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b GlycoTech Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMER; GLYCOCONJUGATE; POLYLYSINE;

ARTICLE; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION;

EID: 0030796980     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970657t     Document Type: Article

References (42)

1. A variety of uses of glycopolymers has recently been summarized in excellent reviews: (a) Roy, R. Trends Glycosci. Glycotech. 1996, 8, 79. (b) Bovin, N. V.; Gabius, H.-J. Chem. Soc. Rev. 1995, 413. (c) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71.
2. A variety of uses of glycopolymers has recently been summarized in excellent reviews: (a) Roy, R. Trends Glycosci. Glycotech. 1996, 8, 79. (b) Bovin, N. V.; Gabius, H.-J. Chem. Soc. Rev. 1995, 413. (c) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71.
3. A variety of uses of glycopolymers has recently been summarized in excellent reviews: (a) Roy, R. Trends Glycosci. Glycotech. 1996, 8, 79. (b) Bovin, N. V.; Gabius, H.-J. Chem. Soc. Rev. 1995, 413. (c) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71.
4. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
5. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
6. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
7. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
8. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
9. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
10. Involving alkenyl glycosides: (a) Horejší, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293. (b) Kochetkov, N. D. Pure Appl. Chem. 1984, 56, 923. (c) Roy, R.; Lafèrriere, C. A.; Gamian, A.; Jennings, H. J. J. Carbohydr. Chem. 1987, 6, 161. (d) Kosma, P.; Strobl, M.; März, L.; Kusumoto, S.; Fukase, K.; Brade, H. Carbohydr. Res. 1993, 238, 93. (e) Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nishi, N.; Tokura, S.; Nagami, K.; Murayama, S.; Kurita, K. Macromolecules 1994, 27, 157. (f) Takeo, K.; Kawaguchi, M.; Kitamura, S. J. Carbohydr. Chem. 1993, 12, 1043. (g) Kobayashi, K.; Akaike, T.; Usui, T. Methods Enzymol. 1994, 242, 226.
11. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
12. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
13. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
14. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
15. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
16. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
17. Involving N-acryloylated glycosides: (a) Lee, R. T.; Lee., Y. C. Carbohydr. Res. 1974, 34, 151. (b) Lee, R. T.; Lee., Y. C. Methods Enzymol. 1982, 83, 299. (c) Roy, R.; Laferrière, C. A. Carbohydr. Res. 1988, 177, C1 (d) Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem. 1992, 104, 1551. (e) Roy, R.; Park, W. K.; Srivastava, O. M.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399. (f) Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. J. Carbohydr. Chem. 1991, 10, 691. (g) Chernyak, A. Y.; Kononov, L. O.; Kochetkov, N. K. J. Carbohydr. Chem. 1994, 13, 383. (h) Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. J. Med. Chem. 1994, 37, 3419.
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36. The addition of thiolated carbohydrates to chloroacetylated dendrimers was used by Roy et al. to prepare carbohydrate clusters by treatment with excess amounts of a thiolated carbohydrate, (a) Zanini, D.; Roy, R. J. Am. Chem. Soc. 1997, 119, 2088 and references cited therein. These relatively small molecules with only 4-16 identical residues are different from our polymers (250 lysine residues) that contain three different residues.
37. n = 1.20. Polylysine is also avalable with different molecular masses and in the D and D/L form.
38. The reaction of 1 with mercapto ethanol gave a poorly water soluble product which was not further characterized.
39. n = 1.40; done by Polymer Standards Service, Postfach 3368, D-55023 Mainz, Germany.
40. 4 and the optical density is determined at 450 nm.
41. Kretzschmar, G.; Toepfer, A.; Huels, C.; Krause, M. Tetrahedron 1997, 53, 2485.
42. a containing polyacrylate derived from 4-nitrophenyl polyacrylate; see ref 4 (Synthesome, Gesellschaft fuer medizinische Biochemie mbH, Heimdall Str. 4, D-81739 Munic, Germany). Weitz-Schmidt, G.; Stockmaier, D.; Scheel, G.; Nifant'ev, N. E.; Tuzikov, A. B.; Bovin, N. V. Anal. Biochem. 1996, 238, 184.