An expeditious click approach towards the synthesis of galactose coated novel glyco-dendrimers and dentromers utilizing a double stage convergent method

• Published in: RSC advances 2020-08, Vol.1 (52), p.31553-31562
• Main Authors: Agrahari, Anand K, Singh, Anoop S, Mukherjee, Rishav, Tiwari, Vinod K
• Format: Article
• Language: English
• Subjects: Alkynes; Chemistry; Coating; Convergence; Cycloaddition; Dendrimers; Galactose; Liquid chromatography; NMR; Nuclear magnetic resonance; Synthesis
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d0ra05289b

The primary motive behind this article is to bring to the forefront a unique kind of dendrimer which has remained a dark horse since its discovery, namely dentromer. We herein report the synthesis of glycodendrimers and glycodentromers crowned with galactose units by harnessing an expeditious synthesis of dendrimer core 18 and dentromer core 19 , divergently with branching directionality (1 → 2) and (1 → 3), respectively. A competent, double stage convergent synthetic path was chosen to facilitate ease of refining and spectroscopic elucidations. By exploiting a Cu( i )-catalyzed azide-alkyne cycloaddition (CuAAC) reaction strategy, we successfully developed a new series of galactosylated dendrimers 20 , 21 , 22 , and 24 containing 6, 12, 18, and 18 peripheral galactose units, respectively. We are first to report the practical synthesis of 9-peripheral galactose coated glycodentromer 23 (0 th generation) and 27-peripheral galactose coated glycodentromer 25 (1 st generation). These synthesized scaffolds were characterized by spectral studies such as 1 H, 13 C NMR, FT-IR, MALDI-TOF MS, HRMS and SEC analysis. Additionally, gel permeation chromatography depicted the regular progression in size from 6 to 27-peripheral galactose coated glycodendrimers along with glycodentromers, with their high monodispersity. Also, the glyco-dendrimers and dentromers synthesized from two different hypercore units i.e. dendrimers core ( 18 ) and dentromer core ( 19 ), have been supported by their UV-visible absorbance and emission spectroscopy. A proficient double stage convergent approach has been exploited for an easy access of galactose coated novel glycodendrimers and dentromers under CuAAC click condition.