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

被引:20
作者
Agrahari, Anand K. [1 ]
Singh, Anoop S. [1 ]
Mukherjee, Rishav [1 ]
Tiwari, Vinod K. [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Ctr Adv Study, Dept Chem, Varanasi 221005, Uttar Pradesh, India
关键词
CHEMISTRY INSPIRED SYNTHESIS; SELECTIVE RECOGNITION; SOLID-PHASE; GLYCODENDRIMERS; DENDRONS; LECA;
D O I
10.1039/d0ra05289b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 core18and dentromer core19, 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 dendrimers20,21,22, and24containing 6, 12, 18, and 18 peripheral galactose units, respectively. We are first to report the practical synthesis of 9-peripheral galactose coated glycodentromer23(0(th)generation) and 27-peripheral galactose coated glycodentromer25(1(st)generation). These synthesized scaffolds were characterized by spectral studies such as(1)H,C-13 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 unitsi.e.dendrimers core (18) and dentromer core (19), have been supported by their UV-visible absorbance and emission spectroscopy.
引用
收藏
页码:31553 / 31562
页数:10
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