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. 2020 Aug 26;10(52):31553-31562.
doi: 10.1039/d0ra05289b. eCollection 2020 Aug 21.

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

Anand K Agrahari  1 , Anoop S Singh  1 , Rishav Mukherjee  1 , Vinod K Tiwari  1
Affiliations

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

Anand K Agrahari et al. RSC Adv. .

Abstract

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 (0th generation) and 27-peripheral galactose coated glycodentromer 25 (1st generation). These synthesized scaffolds were characterized by spectral studies such as 1H, 13C 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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthesis of azide functionalized AB2 and AB3 type dendritic structure.
Scheme 2
Scheme 2. Synthesis of acid functionalized dentritic scaffolds.
Scheme 3
Scheme 3. Synthesis of ester-linked dendrimers core and dentromer core by acid–phenol coupling using DCC/DMAP.
Scheme 4
Scheme 4. Synthesis of galactosylated dendrimer (20, 21 and 22) derived from hexavalent alkyne core 18.
Scheme 5
Scheme 5. CuAAC mediated synthesis of galactose coated dendrimers (23, 24 and 25) derived from dentromer core 19.
Fig. 1
Fig. 1. ‘1H NMR’ spectral elucidation of triazolyl region of first generation glycodentromer.
Fig. 2
Fig. 2. SEC chromatogram of the developed glycodendrimers (20, 21, 22, 24) and glycodentromers (23, 25).
Fig. 3
Fig. 3. Absorbance and emission spectra of the developed glycodendrimers (20, 21, 22, 24) and glycodentromers (23, 25).
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