One-Pot Synthesis and Electrospinning of Cellulose Derivatives Bearing Pseudo-Peptide Pendants via Ugi Four−Component Reaction for Functional Nanofiber Fabrication
Abstract
The one-pot synthesis and electrospinning of cellulose derivatives bearing pseudo-peptide pendants, which are expected to serve as novel chiral recognition materials, are reported. Ugi four-component reactions (U-4CRs) involving carboxymethyl cellulose (CMC), formaldehyde, a glycine-based isocyanide (ethyl isocyanoacetate), and six different amino acid methyl esters as the carboxylic acid, aldehyde, isocyanide, and amine components, respectively, were employed to introduce pseudo-peptide pendants onto the cellulose backbone. The reactions proceeded successfully under weakly acidic conditions (pH 4), yielding derivatives with degrees of substitution (DSs) of 0.37−0.44, whereas reactions at pH 1−3 and 5 were hindered by competing side reactions. The derivatives were characterized by FTIR, NMR, size-exclusion chromatography, and elemental analysis. Furthermore, they were successfully electrospun using poly(ethylene oxide) as a carrier polymer, producing uniform and continuous nanofibers. These results demonstrate the feasibility of combining U−4CR with electrospinning to fabricate functional cellulose-based nanofibrous materials for potential chiral recognition applications.
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BibTeX
@article{nonotagne2026onepot,
title = {{One-Pot Synthesis and Electrospinning of Cellulose Derivatives Bearing Pseudo-Peptide Pendants via Ugi Four−Component Reaction for Functional Nanofiber Fabrication}},
author = {Steve Nono-Tagne and Minoru Kuroiwa and Mihaela Ciorescu and Maëlle Fischer and Isabelle Jeacomine and Jean-Luc Putaux and Yoshiharu Nishiyama and Atsushi Narumi and Ryohei Kakuchi and Issei Otsuka},
journal = {Biomacromolecules},
year = {2026},
month = sep,
doi = {10.1021/acs.biomac.6c01517},
url = {https://hal.science/hal-05771981v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - One-Pot Synthesis and Electrospinning of Cellulose Derivatives Bearing Pseudo-Peptide Pendants via Ugi Four−Component Reaction for Functional Nanofiber Fabrication
AU - Steve Nono-Tagne
AU - Minoru Kuroiwa
AU - Mihaela Ciorescu
AU - Maëlle Fischer
AU - Isabelle Jeacomine
AU - Jean-Luc Putaux
AU - Yoshiharu Nishiyama
AU - Atsushi Narumi
AU - Ryohei Kakuchi
AU - Issei Otsuka
PY - 2026
DA - 2026/09/24
JO - Biomacromolecules
DO - 10.1021/acs.biomac.6c01517
UR - https://hal.science/hal-05771981v1
AB - The one-pot synthesis and electrospinning of cellulose derivatives bearing pseudo-peptide pendants, which are expected to serve as novel chiral recognition materials, are reported. Ugi four-component reactions (U-4CRs) involving carboxymethyl cellulose (CMC), formaldehyde, a glycine-based isocyanide (ethyl isocyanoacetate), and six different amino acid methyl esters as the carboxylic acid, aldehyde, isocyanide, and amine components, respectively, were employed to introduce pseudo-peptide pendants onto the cellulose backbone. The reactions proceeded successfully under weakly acidic conditions (pH 4), yielding derivatives with degrees of substitution (DSs) of 0.37−0.44, whereas reactions at pH 1−3 and 5 were hindered by competing side reactions. The derivatives were characterized by FTIR, NMR, size-exclusion chromatography, and elemental analysis. Furthermore, they were successfully electrospun using poly(ethylene oxide) as a carrier polymer, producing uniform and continuous nanofibers. These results demonstrate the feasibility of combining U−4CR with electrospinning to fabricate functional cellulose-based nanofibrous materials for potential chiral recognition applications.
SN - 1525-7797
SN - 1526-4602
ER -