Application

No.134
Monoaminated & Monotosylated Cyclodextrins
A1916 3A-Amino-3A-deoxy-(2AS,3AS)-β-cyclodextrin Hydrate 1g
M1741 Mono-2-O-(p-toluenesulfonyl)-β-cyclodextrin 1g
M1644 Mono-6-O-(p-toluenesulfonyl)-α-cyclodextrin 200mg
M1645 Mono-6-O-(p-toluenesulfonyl)-γ-cyclodextrin 200mg

Cyclodextrin (CD) is a cyclic oligosaccharide composed of α-1,4 linked glucose and it takes a conic trapezoid form. The inside of this conic trapezoid is a three-dimensional cavity, which will take a guest molecule to fit this cavity size to form a clathrate compound. These clathrate phenomena are utilized in various fields such as foods, cosmetics, separation analysis, etc.

In recent years, there has been much research into CD derivatives having the clathrate ability, but to which a new function is added by introducing functional molecules to a certain position within CD. For example, CD bearing a fluorescent dye moiety as a molecular recognition fluorescent sensor,1) CD bearing C602) as water soluble C60, and CD bearing trypsin3) as stabilized trypsin have been reported. As starting materials for the synthesis of these CD derivatives, CD having a certain hydroxyl group, which is activated,4) and CD having a certain hydroxyl group converted to an amino group are used.

We have commercially produced CD derivatives in which the primary hydroxyl group at the 6 position of CD is converted to tosyloxy group, the secondary hydroxyl group at the 2 position is converted to tosyloxy group, and the steric configuration of the second hydroxyl group at the 3 position is inverted and converted to an amino group. We hope you will find these materials useful for the synthesis of, and research into, these functional CD derivatives.

References

1) A modified cyclodextrin as a guest responsive colour-change indicator
A. Ueno, T. Kuwabara, A. Nakamura, F. Toda, Nature, 1992, 356, 136; K. Hamasaki, H. Ikeda, A.Nakamura, A. Ueno, F. Toda, I. Suzuki, T. Osa, J. Am. Chem. Soc., 1993, 115, 5035; M. Narita, S. Mima, N. Ogawa, F. Hamada, Anal. Sci., 2000, 16, 865.
2) Synthesis of water-soluble cyclodextrin-C60 conjugates
S. Samal, K. E. Geckeler, Synth. Commun., 2002, 32, 3367; C. Yong, W. Yali, R. Andre, S. Pierre, Z. Yu, Z. Yongmin, Tetrahedron, 2006, 62, 2045.
3) Improved functional properties of trypsin modified by cyclodextrin derivatives
F. Michael, F. Alex, C. Robert, V. Reynaldo, J. Mol. Catal B, Enzyme, 2003, 21, 133.
4) Monotosylated cyclodextrins
T. Kaneda, T. Fujimoto, J. Goto, K. Asano, Y. Yasufuku, J. H. Jung, C. Hosono, Y. Sakata, Chem. Lett., 2002, 514.
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