Using cellulose, starch and β-cyclodextrin poly/oligosaccharides as chiral inducers for preparing chiral particles

Huli Yu; Liangjie Wang; Sheng Liu; Biao Zhao; Ke Xiao; Bo Yang; Huabo Duan; Huazhang Zhao; Jianping Deng

doi:10.1016/j.carbpol.2022.119944

Using cellulose, starch and β-cyclodextrin poly/oligosaccharides as chiral inducers for preparing chiral particles

Carbohydr Polym. 2022 Nov 15:296:119944. doi: 10.1016/j.carbpol.2022.119944. Epub 2022 Aug 2.

Authors

Huli Yu¹, Liangjie Wang¹, Sheng Liu², Biao Zhao³, Ke Xiao⁴, Bo Yang⁵, Huabo Duan⁶, Huazhang Zhao⁷, Jianping Deng⁸

Affiliations

¹ College of Civil and Transportation Engineering, Shenzhen University, Shenzhen 518060, PR China; Water Science and Environmental Engineering Research Center, College of Chemical and Environmental Engineering, Shenzhen University, Shenzhen 518060, PR China; The Key Laboratory of Water and Sediment Sciences (Ministry of Education), College of Environmental Sciences and Engineering, Peking University, Beijing 100871, PR China.
² The Key Laboratory of Water and Sediment Sciences (Ministry of Education), College of Environmental Sciences and Engineering, Peking University, Beijing 100871, PR China.
³ State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, PR China.
⁴ Water Science and Environmental Engineering Research Center, College of Chemical and Environmental Engineering, Shenzhen University, Shenzhen 518060, PR China. Electronic address: xiaoke@szu.edu.cn.
⁵ Water Science and Environmental Engineering Research Center, College of Chemical and Environmental Engineering, Shenzhen University, Shenzhen 518060, PR China.
⁶ College of Civil and Transportation Engineering, Shenzhen University, Shenzhen 518060, PR China.
⁷ The Key Laboratory of Water and Sediment Sciences (Ministry of Education), College of Environmental Sciences and Engineering, Peking University, Beijing 100871, PR China; Shanxi Laboratory for Yellow River, Shanxi University, Taiyuan 030006, PR China. Electronic address: zhaohuazhang@pku.edu.cn.
⁸ State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, PR China. Electronic address: dengjp@mail.buct.edu.cn.

PMID: 36087992
DOI: 10.1016/j.carbpol.2022.119944

Abstract

Poly/oligosaccharides are renewable natural resources with abundant chirality. Herein, we develop a general route to prepare optically active particles by using poly/oligosaccharides as both chiral inducers and growth templates. By complexing with Cu(NH₃)₄²⁺ ions, OH groups on C2 and C3 in poly/oligosaccharides can transfer the chirality to Cu(II) and retain it in CuO. At the same time, poly/oligosaccharides direct growth of CuO by in situ transformation of Cu(NH₃)₄²⁺ ions. Cellulose nanocrystal (CNC) and starch (ST) are used as representative polysaccharides, and β-cyclodextrin (β-CD) as a representative oligosaccharide, thus dandelion, duchesnea, and chrysanthemum-like composite particles with chiroptical activity are obtained. Besides, chiral CuO/poly(oligo)saccharide particles (CSP) demonstrate enantioselective ability by differentiating coordination with tryptophan (Trp) enantiomers and form Cu-Trp metal organic framework architectures with different morphologies. The study provides an easily accessible approach to prepare novel functional materials by poly/oligosaccharide-based chiral induction and hold great promise in chiral applications.

Keywords: Chiral induction; Chiral recognition; Enantio-differentiating coordination; Optically active particles; Poly/oligosaccharides.

MeSH terms

Cellulose* / chemistry
Oligosaccharides
Starch
Stereoisomerism
Tryptophan
beta-Cyclodextrins* / chemistry

Substances

Oligosaccharides
beta-Cyclodextrins
Tryptophan
Cellulose
Starch