Bio-synthetic Polymer Conjugates by Helmut Schlaad
Author:Helmut Schlaad
Language: eng
Format: epub
Publisher: Springer Berlin Heidelberg, Berlin, Heidelberg
The efficiency of Click coupling reactions was shown by the work of Hawker and coworkers [196] on the synthesis of asymmetric dendrimers from unprotected azido-sugars and alkyne-terminated dendrimers. The produced materials contained multiple functionalities (carbohydrate and fluorophore).
Riguera et al. [197] reported the conjugation of unprotected alkyne-derived carbohydrates to dendritic systems incorporating terminal azides using Click chemistry in combination with ultrafiltration, as opposed to the lengthier process of employing protected glycosides or introducing the Click functionality on each generation of previously synthesized dendrimers (Scheme 11). It was also shown that the reported procedure is quick, efficient, and reliable, allowing the incorporation of up to 27 unprotected fucose, mannose, and lactose residues in reproducible high yields (up to 92%), requiring only catalytic amounts of Cu. Both 1H-NMR and MALDI-TOF MS were used to establish the completion of the conjugation process [197].
Scheme 11Synthesis of different glycodendrimers via Click chemistry. Reprinted from [197] with permission. Copyright 2006, American Chemical Society
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