Glycolipids from Candida bombicola: Polymerization of a 6-O-acryloyl sophorolipid derivative

Macromolecules

Volumn 33, Issue 17, 2000, Pages 6208-6210

  Bisht, Kirpal S ^a,b   Gao, Wei ^a   Gross, Richard A ^a  

^a POLYTECHNIC UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMERS; ENZYMES; GEL PERMEATION CHROMATOGRAPHY; LIPIDS; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYSACCHARIDES; SYNTHESIS (CHEMICAL);

CHEMOENZYMATIC METHOD; GLYCOLIPIDS; SOPHOROLIPIDS;

MACROMOLECULES;

EID: 0034702624     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0001537     Document Type: Article

References (26)

1. Malm, C. J.; Meneh, J. W.; Kendall, D. L.; Hiatt, G. D. Ind. Eng. Chem. 1951, 43, 684. Matsumura, S. J. Environ. Polym. Deg. 1994, 2, 89, Wang, P.; Tao, B. Y. J. Appl. Polym. Sci. 1994, 52, 755. Nishio, K.; Nakaya, T.; Imoto, M. Makromol. Chem. 1974, 175, 3319. Carpino, L. A.; Ringsdrof, H.; Ritter, H. Mackromol. Chem. 1976, 177, 1631.
2. Malm, C. J.; Meneh, J. W.; Kendall, D. L.; Hiatt, G. D. Ind. Eng. Chem. 1951, 43, 684. Matsumura, S. J. Environ. Polym. Deg. 1994, 2, 89, Wang, P.; Tao, B. Y. J. Appl. Polym. Sci. 1994, 52, 755. Nishio, K.; Nakaya, T.; Imoto, M. Makromol. Chem. 1974, 175, 3319. Carpino, L. A.; Ringsdrof, H.; Ritter, H. Mackromol. Chem. 1976, 177, 1631.
3. Malm, C. J.; Meneh, J. W.; Kendall, D. L.; Hiatt, G. D. Ind. Eng. Chem. 1951, 43, 684. Matsumura, S. J. Environ. Polym. Deg. 1994, 2, 89, Wang, P.; Tao, B. Y. J. Appl. Polym. Sci. 1994, 52, 755. Nishio, K.; Nakaya, T.; Imoto, M. Makromol. Chem. 1974, 175, 3319. Carpino, L. A.; Ringsdrof, H.; Ritter, H. Mackromol. Chem. 1976, 177, 1631.
4. Malm, C. J.; Meneh, J. W.; Kendall, D. L.; Hiatt, G. D. Ind. Eng. Chem. 1951, 43, 684. Matsumura, S. J. Environ. Polym. Deg. 1994, 2, 89, Wang, P.; Tao, B. Y. J. Appl. Polym. Sci. 1994, 52, 755. Nishio, K.; Nakaya, T.; Imoto, M. Makromol. Chem. 1974, 175, 3319. Carpino, L. A.; Ringsdrof, H.; Ritter, H. Mackromol. Chem. 1976, 177, 1631.
5. Malm, C. J.; Meneh, J. W.; Kendall, D. L.; Hiatt, G. D. Ind. Eng. Chem. 1951, 43, 684. Matsumura, S. J. Environ. Polym. Deg. 1994, 2, 89, Wang, P.; Tao, B. Y. J. Appl. Polym. Sci. 1994, 52, 755. Nishio, K.; Nakaya, T.; Imoto, M. Makromol. Chem. 1974, 175, 3319. Carpino, L. A.; Ringsdrof, H.; Ritter, H. Mackromol. Chem. 1976, 177, 1631.
6. Treadway, R. H.; Yanovsky, E. J. Am. Chem. Soc. 1945, 67, 1038. Haworth, W. N.; Gregory, H.; Wiggins, L. F. J. Chem. Soc. 1946, 489.
7. Treadway, R. H.; Yanovsky, E. J. Am. Chem. Soc. 1945, 67, 1038. Haworth, W. N.; Gregory, H.; Wiggins, L. F. J. Chem. Soc. 1946, 489.
8. Sugihara, J. M. Adv. Carbohydr. Chem. 1953, 8, 1. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11. Wolfrom, M. L.; Szarek, W. A. In The Carbohydrates Chemistry and Biochemistry, 2nd ed.; Pigman, W., Horton, D., Eds.; Academic Press: New York, 1972; Vol. IA, pp 217-251. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1981, 39, 13.
9. Sugihara, J. M. Adv. Carbohydr. Chem. 1953, 8, 1. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11. Wolfrom, M. L.; Szarek, W. A. In The Carbohydrates Chemistry and Biochemistry, 2nd ed.; Pigman, W., Horton, D., Eds.; Academic Press: New York, 1972; Vol. IA, pp 217-251. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1981, 39, 13.
10. Sugihara, J. M. Adv. Carbohydr. Chem. 1953, 8, 1. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11. Wolfrom, M. L.; Szarek, W. A. In The Carbohydrates Chemistry and Biochemistry, 2nd ed.; Pigman, W., Horton, D., Eds.; Academic Press: New York, 1972; Vol. IA, pp 217-251. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1981, 39, 13.
11. Sugihara, J. M. Adv. Carbohydr. Chem. 1953, 8, 1. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1976, 33, 11. Wolfrom, M. L.; Szarek, W. A. In The Carbohydrates Chemistry and Biochemistry, 2nd ed.; Pigman, W., Horton, D., Eds.; Academic Press: New York, 1972; Vol. IA, pp 217-251. Haines, A. H. Adv. Carbohydr. Chem. Biochem. 1981, 39, 13.
12. Martin, B. D.; Lindhart, R. J. Biomaterials 1998, 19, 76. Chen, X. M.; Johnson, A Macromol. Chem. Phys. 1994, 195, 3567. Patil, D. R.; Dordick, J. S.; Rethwisch, D. G. Macromolecules 1991, 24, 3462. Klibanov, A. M. Biotechnol. Bioeng. 1987, 29, 648.
13. Martin, B. D.; Lindhart, R. J. Biomaterials 1998, 19, 76. Chen, X. M.; Johnson, A Macromol. Chem. Phys. 1994, 195, 3567. Patil, D. R.; Dordick, J. S.; Rethwisch, D. G. Macromolecules 1991, 24, 3462. Klibanov, A. M. Biotechnol. Bioeng. 1987, 29, 648.
14. Martin, B. D.; Lindhart, R. J. Biomaterials 1998, 19, 76. Chen, X. M.; Johnson, A Macromol. Chem. Phys. 1994, 195, 3567. Patil, D. R.; Dordick, J. S.; Rethwisch, D. G. Macromolecules 1991, 24, 3462. Klibanov, A. M. Biotechnol. Bioeng. 1987, 29, 648.
15. Martin, B. D.; Lindhart, R. J. Biomaterials 1998, 19, 76. Chen, X. M.; Johnson, A Macromol. Chem. Phys. 1994, 195, 3567. Patil, D. R.; Dordick, J. S.; Rethwisch, D. G. Macromolecules 1991, 24, 3462. Klibanov, A. M. Biotechnol. Bioeng. 1987, 29, 648.
16. Martin, B. D.; Ampofo, S. A.; Linhardt, R. J.; Dordick, J. S. Macromolecules 1992, 25, 7081. Ikeda, I.; Klibanov, A. M. Biotechnol. Bioeng. 1993, 42, 788.
17. Martin, B. D.; Ampofo, S. A.; Linhardt, R. J.; Dordick, J. S. Macromolecules 1992, 25, 7081. Ikeda, I.; Klibanov, A. M. Biotechnol. Bioeng. 1993, 42, 788.
18. Klibanov, A. M. CHEMTECH 1986, 16, 354.
19. Gorin, A. P. J.; Spenser, J. F. T.; Tulloch, A. P. Can. J. Chem. 1961, 39, 846.
20. Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780.
21. 5 (0.1 mmHg, 25 °C, 16 h).
22. Synthesized from 1 by Novozym 435 catalyzed acryloylation with vinyl acrylate. In a representative example: A solution of 1.3 g of 1 and 2.5 mL of vinyl acrylate in 30 mL of THF was stirred magnetically at 35 °C for 96 h in the presence of 3 g of Novozym 435. The reaction setup secluded from the light and followed by TLC. The reaction was quenched by removing the enzyme by vacuum filtration. The solvent was removed in vacuo to give 1.5 g of the crude biotransformation product, which was purified by column chromatography over silica gel to give 1.2 g of purified 2.
23. 13C NMR spectra were recorded at 62.9 or 125.7 MHz with chemical shifts in ppm referenced relative to TMS at 0.00 ppm.
24. CHN analyses were performed in duplicate at Atlantic Microlabs, Inc., Georgia.
25. A 2 N NaOH solution (3 mL) was added to 4 mg of the polymer sample. The reaction vial was sealed and kept at 55 °C for 24 h. Dilute HCl solution was used to neutralize the reaction mixture to pH = 7. The polymer samples were recovered after removing water in vacuo at 55 °C.
26. n = 1.2.