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Title: Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly

Abstract

Due to the branched structure feature and unique properties, a variety of star-shaped polymers have been designed and synthesized. Despite those advances, solid-phase synthesis of star-shaped sequence-defined synthetic polymers that exhibit hierarchical self-assembly remains a significant challenge. Hence, we present an effective strategy for the solid-phase synthesis of three-armed star-shaped peptoids, in which ethylenediamine was used as the centric star pivot. Based on the sequence of monomer addition, a series of AA'A''-type and ABB'-type peptoids were synthesized and characterized by UPLC-MS (ultra-high performance liquid chromatography-mass spectrometry). By taking advantage of the easy-synthesis and large side-chain diversity, we synthesized star-shaped peptoids with tunable functions. We further demonstrated the aqueous self-assembly of some representative peptoids into biomimetic nanomaterials with well-defined hierarchical structures, such as nanofibers and nanotubes. These results indicate that star-shaped peptoids offer the potential in self-assembly of biomimetic nanomaterials with tunable chemistries and functions.

Authors:
ORCiD logo [1];  [1];  [2];  [1];  [3];  [2];  [1]
  1. BATTELLE (PACIFIC NW LAB)
  2. UNIVERSITY PROGRAMS
  3. MULTIPLE CONTRACTORS
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1530730
Report Number(s):
PNNL-SA-140649
DOE Contract Number:  
AC05-76RL01830
Resource Type:
Journal Article
Journal Name:
Biopolymers
Additional Journal Information:
Journal Volume: 110; Journal Issue: 4
Country of Publication:
United States
Language:
English
Subject:
Solid-phase synthesis, star-shaped peptoids, aqueous self-assembly, biomimetic nanomaterials

Citation Formats

Jin, Haibao, Jian, Teng-Yue, Ding, Yanhuai, Chen, Yulin, Mu, Peng, Wang, Lei, and Chen, Chunlong. Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly. United States: N. p., 2019. Web. doi:10.1002/bip.23258.
Jin, Haibao, Jian, Teng-Yue, Ding, Yanhuai, Chen, Yulin, Mu, Peng, Wang, Lei, & Chen, Chunlong. Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly. United States. doi:10.1002/bip.23258.
Jin, Haibao, Jian, Teng-Yue, Ding, Yanhuai, Chen, Yulin, Mu, Peng, Wang, Lei, and Chen, Chunlong. Mon . "Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly". United States. doi:10.1002/bip.23258.
@article{osti_1530730,
title = {Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly},
author = {Jin, Haibao and Jian, Teng-Yue and Ding, Yanhuai and Chen, Yulin and Mu, Peng and Wang, Lei and Chen, Chunlong},
abstractNote = {Due to the branched structure feature and unique properties, a variety of star-shaped polymers have been designed and synthesized. Despite those advances, solid-phase synthesis of star-shaped sequence-defined synthetic polymers that exhibit hierarchical self-assembly remains a significant challenge. Hence, we present an effective strategy for the solid-phase synthesis of three-armed star-shaped peptoids, in which ethylenediamine was used as the centric star pivot. Based on the sequence of monomer addition, a series of AA'A''-type and ABB'-type peptoids were synthesized and characterized by UPLC-MS (ultra-high performance liquid chromatography-mass spectrometry). By taking advantage of the easy-synthesis and large side-chain diversity, we synthesized star-shaped peptoids with tunable functions. We further demonstrated the aqueous self-assembly of some representative peptoids into biomimetic nanomaterials with well-defined hierarchical structures, such as nanofibers and nanotubes. These results indicate that star-shaped peptoids offer the potential in self-assembly of biomimetic nanomaterials with tunable chemistries and functions.},
doi = {10.1002/bip.23258},
journal = {Biopolymers},
number = 4,
volume = 110,
place = {United States},
year = {2019},
month = {4}
}

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