231
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Glucosylation of Sucrose Laurate with Cyclodextrin Glucanotransferase

, , , &
Pages 826-829 | Received 15 Nov 2006, Accepted 22 Nov 2006, Published online: 22 May 2014

  • 1) Nakamura, S., Using sucrose esters as food emulsifiers. Oleochemicals, 8, 866–874 (1997).
  • 2) Chen, J., Kimura, Y., and Adachi, S., Synthesis of linoleoyl disaccharides through lipase-catalyzed condensation and their surface activities. J. Biosci. Bioeng., 100, 274–279 (2005).
  • 3) Hill, K., and Rhode, O., Sugar-based surfactants for consumer products and technical applications. Lipid - Fett., 101, 25–33 (1999).
  • 4) Gandhi, N. N., Patil, N. S., Sawant, S. B., Joshi, J. B., Wangikar, P. P., and Mukesh, D., Lipase-catalyzed esterification. Cat. Rev., 42, 439–480 (2000).
  • 5) Potier, P., Bouchu, A., Gagnaire, J., and Queneau, Y., Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides. Tetrahedron: Asymmetry, 12, 2409–2419 (2001).
  • 6) Kometani, T., Terada, Y., Nishimura, T., Takii, H., and Okada, S., Synthesis of hesperidin glycosides by cyclodextrin glucanotransferase from an alkalophilic Bacillus species in alkaline pH and properties of hesperidin glucosides. Biosci. Biotechnol. Biochem., 58, 1990–1994 (1994).
  • 7) Ferrer, M., Cruces, M. A., Bernabe, M., Ballesteros, A., and Plou, F. J., Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures. Biotechnol. Bioeng., 65, 10–16 (1999).
  • 8) Plou, F. J., Cruces, M. A., Pastor, E., Ferrer, M., Bernabe, M., and Ballesterose, A., Acylation of sucrose with vinyl esters using immobilized hydrolases: demonstration that chemical catalysis may interfere with enzymatic catalysis. Biotechnol. Lett., 21, 635–639 (1999).
  • 9) Polat, T., and Linhardt, R. J., Synthesis and applications of sucrose-based esters. J. Surf. Deterg., 4, 415–421 (2001).
  • 10) (4): 1H NMR δH (CD3OD): 0.84 (3H, t, J=6.9 Hz, CH3), 1.24 (16H, m, 8×CH2), 1.56 (2H, m, β-CH2 from C=O), 2.29 (2H, m, α-CH2–C=O), 3.20–4.33 (27H, m, protons on sugar moiety), 5.13 (1H, d, J=3.9 Hz, an anomeric proton on the first pyranose ring from the glucose in the sucrose structure), 5.29 (1H, d, J=3.9 Hz, an anomeric proton on the glucose next to the furanose ring). 13C NMR δC (CD3OD): 13.2 (CH3), 21.6–28.6 (8×CH2), 30.9 (β-CH2 from C=O), 32.9 (α-CH2–C=O), 59.3–78.6 (15 carbons in the sugar moiety), 101.5–101.8 (2 anomeric carbons), 104.5 (2′-carbon in the furanose ring), 173.5 (C=O). (5): 1H NMR δH (CD3OD): 0.79 (3H, t, J=6.9 Hz, CH3), 1.19 (16H, m, 8×CH2), 1.51 (2H, m, β-CH2 from C=O), 2.24 (2H, m, α-CH2–C=O), 3.18 (1H, dd, J=9.3 Hz, proton at the non-reducing terminal on the second pyranose ring from the sucrose), 3.19–4.28 (27H, m, protons in sugar moiety), 5.06 and 5.09 (2H, d, J=3.9 Hz, anomeric protons on the first and second pyranose rings from the glucose in the sucrose structure), 5.24 (1H, d, J=3.9 Hz, an anomeric proton on the glucose next to the furanose ring). 13C NMR δC (CD3OD): 13.2 (CH3), 21.6–28.7 (8×CH2), 30.9 (β-CH2 from C=O), 32.9 (α-CH2–C=O), 58.1–79.4 (20 carbons in the sugar moiety), 100.8–101.4 (3 anomeric carbons), 104.1 (2′-carbon in the furanose ring), 173.5 (C=O). (6): 1H NMR δH (CD3OD): 0.79 (3H, t, J=6.9 Hz, CH3), 1.19 (16H, m, 8×CH2), 1.52 (2H, m, β-CH2 from C=O), 2.26 (2H, m, α-CH2–C=O), 3.16 (1H, m, proton at the non-reducing terminal of the glucose moiety next to sucrose), 3.20–4.53 (18H, m, protons on sugar moiety), 5.03 (1H, d, J=3.9 Hz, an anomeric proton on the first pyranose ring from the glucose in the sucrose structure), 5.28 (1H, d, J=3.9 Hz, an anomeric proton on the glucose next to the furanose ring). 13C NMR δC (CD3OD): 12.9 (CH3), 21.7–28.8 (8×CH2), 31.1 (β-CH2 from C=O), 33.0 (2H, m, α-CH2–C=O), 59.6–94.3 (15 carbons in the sugar moiety), 100.8–102.1 (2 anomeric carbons), 103.5 (2′-carbon in the furanose ring), 173.5 (C=O). (7): 1H NMR δH (CD3OD): 0.78 (3H, t, J=6.9 Hz, CH3), 1.16 (16H, m, 8×CH2), 1.49 (2H, m, β-CH2 from C=O), 2.26 (2H, m, α-CH2–C=O), 3.13–4.23 (28H, m, protons on sugar carbons), 3.98 (1H, m, a proton at 5-carbon in pyranose ring of sucrose), 4.26 (1H, d, J=12 Hz, a proton at 3-carbon in pyranose ring of sucrose), 4.54 (1H, m, a proton at 2-carbon in pyranose ring of sucrose), 5.02 and 5.06 (2H, d, J=3.9 Hz, anomeric protons on the second and third pyranose rings from the glucose in the sucrose structure), 5.13 (1H, d, J=3.9 Hz, an anomeric proton on the first pyranose ring from the glucose in the sucrose structure), 5.25 (1H, d, J=3.9 Hz, anomeric proton on the glucose next to the furanose ring). 13C NMR δC (CD3OD): 12.5 (CH3), 2.... (Remark: This note is truncated in the html because it exceeds the limit of the system (4000 characters per note). The complete text is given in the pdf.)

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.