G Model
CCLET 4751 No. of Pages 5
Chinese Chemical Letters
Communication
The effect of monosaccharides on self-assembly of
benzenetricarboxamides
*
Jue Wang, Wenjing Qi, Guosong Chen
The State Key Laboratory of Molecular Engineering of Polymers and Department of Macromolecular Science, Fudan University, Shanghai 200438, China
A R T I C L E I N F O
A B S T R A C T
Article history:
The interaction between monosaccharides exhibits an important role in the assembly of monosaccha-
ride-containing molecules. In this work, three common monosaccharides, glucose, galactose and
mannose, are employed to investigate the effect of monosaccharide on the self-assembly of
benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three
benzenetricarboxamide derivatives aggregate into different ordered structures. When alanine linkers are
introduced to these molecules between the core and the monosacchride, morphologies of three types of
monosaccharide BTAs turned to disordered, meanwhile their structures become similar with the increase
of the length of alanine linkers, indicating the disappearance of the monosaccharide effects.
© 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Published by Elsevier B.V. All rights reserved.
Received 30 September 2018
Received in revised form 27 November 2018
Accepted 12 December 2018
Available online xxx
Keywords:
Monosaccharide
Self-assembly
Benzenetricarboxamide
Dynamic light scatting (DLS)
Depolarized dynamic light scatting (DDLS)
Carbohydrates are an important type of biomacromolecules in
nature. The basic building blocks of carbohydrates are mono-
saccharides, which commonly exist as pyranose ring structure in
nature. It is well known that the common monosaccharides are
stereoisomers, for example, glucose, galactose and mannose are
stereoisomers with only difference coming from the orientation of
hydroxyl groups. But these differences change the intermolecular
hydrogen bonds between carbohydrates, resulting different
carbohydrate-carbohydrate interactions (CCI). In our previous
studies, we noticed this phenomenon and constructed various
glycopolymers to demonstrate the different properties oriented
from carbohydrates [1–5]. For example, we found that with
crystalline polymeric backbones, mannoside modification helped
the polymer to maintain its crystalline nature, while galactoside
modification made the crystalline polymer become amorphous [5].
Besides, glucoside or galactoside modifications would also equip
polymers with various assembling morphologies and special
biological applications [3,6]. To further decipher the role of
monosaccharides, in this work we tend to employ small molecular
systems to study the effect of various monosaccharides on self-
assembly.
small molecules (such as glycolipid [7,8] and monosaccharide-
containing perylene bisimide derivative [9–11]) have been
employed to study the effect of monosaccharide, but these
compounds showed relatively low carbohydrate content and
monotonous assembly morphology. Thus, we pursued a small
molecular system with relatively high carbohydrate content,
probable abundant assembly morphology and length-adjustable
linkers. BTAs are regarded as one of the most popular supramo-
lecular monomers which can assemble into abundant nano-
structures [12–15]. With hydrophobic interactions and hydrogen
bonds of this small molecule, BTAs favor to assemble into
nanofibers, as a stable and common morphology of assemblies.
Meanwhile, the morphologies could be regulated by inducing
different side chains, forming various helical nanofibers. The
stability and variety of BTA assemblies indicated this small
molecular structure was appropriate to investigate the effect of
monosaccharides. What is more, one BTA molecule could link three
monosaccharides, the high monosaccharide content is beneficial to
amplify the monosaccharide effect on assemblies. In 2016, Meijer
et al. investigated the synthesis and the assembly of monosaccha-
ride-containing BTAs which had a long alkyl chain between
carbohydrate and BTA cores [16]. With different monosaccharides,
all the BTAs assembled into similar nanofibers, indicating that
monosaccharide made little contribution to the assembly mor-
phology. Thus in this paper, we design a new monosaccharide-
containing BTA, in which carbohydrates are linked to the core of
BTA by amide bonds. Three monosaccharides (glucose/Glc,
galactose/Gal and mannose/Man) were connected to the same
BTA core, forming three different molecules (Fig. 1), C(Glc)3, C
For the investigation of monosaccharide on self-assembly, we
chose a small molecule, 1,3,5-benzenetricarboamides (BTAs), to
perform the research on monosaccharide effect on self-assembly. It
should be noticed that some common monosaccharide-containing
* Corresponding author.
1001-8417/© 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
Please cite this article in press as: J. Wang, et al., The effect of monosaccharides on self-assembly of benzenetricarboxamides, Chin. Chem. Lett.