Parrot-Lopez and coworkers reported a strategy of using per-(C-6)-amino
β-CD 74 as a core, after a peptide formation reaction with 75 to afford a
hepta-β-Gal β-CD derivative, 76, which could be recognized by the galactosespecific lectin from Kluyveromyces bulgaricus yeast cells (KbCWL) [49, 50]
(Scheme 16).
14.3.2.4 Dual-Face-Substituted “Bouquet-Type” Glycoclusters
Ortiz Mellet and coworkers employed β-CD as a platform to introduce two
alkynes at the OH-6 and OH-3 positions, followed by Sonogashira crosscoupling or a “click” reaction to afford a tetradecavalent α-Man conjugate. The
iminosugar with the C9 spacer (79, n = 8) exhibited the greatest multivalent
effect against Jack bean α-mannosidase activity of 0.022 mM, as compared with
188–204 mM for monovalent 1-deoxynojirimycin, a nitrogen-containing
glycomimetic, indicating affinity enhancement by four orders of magnitude
[51] (Scheme 17).
Fig. 7 Taxotere delivered by a cyclodextrin-based targeted shuttle [38b]
404
J. Liu et al.
β-CD 74 as a core, after a peptide formation reaction with 75 to afford a
hepta-β-Gal β-CD derivative, 76, which could be recognized by the galactosespecific lectin from Kluyveromyces bulgaricus yeast cells (KbCWL) [49, 50]
(Scheme 16).
14.3.2.4 Dual-Face-Substituted “Bouquet-Type” Glycoclusters
Ortiz Mellet and coworkers employed β-CD as a platform to introduce two
alkynes at the OH-6 and OH-3 positions, followed by Sonogashira crosscoupling or a “click” reaction to afford a tetradecavalent α-Man conjugate. The
iminosugar with the C9 spacer (79, n = 8) exhibited the greatest multivalent
effect against Jack bean α-mannosidase activity of 0.022 mM, as compared with
188–204 mM for monovalent 1-deoxynojirimycin, a nitrogen-containing
glycomimetic, indicating affinity enhancement by four orders of magnitude
[51] (Scheme 17).
Fig. 7 Taxotere delivered by a cyclodextrin-based targeted shuttle [38b]
404
J. Liu et al.