Submonomer synthesis of sequence defined peptoids with diverse side-chains.
Abstract
Peptoids are a diverse family of sequence-defined oligomers of N-substituted glycine monomers, that can be readily accessed by the solid-phase submonomer synthesis method. Due to the versatility and efficiency of this chemistry, and the easy access to hundreds of potential monomers, there is an enormous potential sequence space that can be explored. This has enabled researchers from many different fields to custom-design peptoid sequences tailored to a wide variety of problems in biomedicine, nanoscience and polymer science. Here we provide detailed protocols for the synthesis of peptoids, using optimized protocols that can be performed by non-chemists. The submonomer method is fully compatible with Fmoc-peptide synthesis conditions, so the method is readily automated on existing automated peptide synthesizers using protocols provided here. Although the submonomer synthesis for peptoids is well established, there are special considerations required in order to access many of the most useful and desirable sidechains. Here we provide methods to include most of the amino-acid-like side chains, some of the most important non-natural monomer classes, as well as the creation of peptoid conjugates and peptide-peptoid hybrids.
- Authors:
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1845665
- DOE Contract Number:
- AC02-05CH11231
- Resource Type:
- Book
- Resource Relation:
- Related Information: Book Title: Methods in Enzymology
- Country of Publication:
- United States
- Language:
- English
Citation Formats
Connolly, Michael D, Xuan, Sunting, Molchanova, Natalia, and Zuckermann, Ronald N. Submonomer synthesis of sequence defined peptoids with diverse side-chains.. United States: N. p., 2021.
Web. doi:10.1016/bs.mie.2021.04.022.
Connolly, Michael D, Xuan, Sunting, Molchanova, Natalia, & Zuckermann, Ronald N. Submonomer synthesis of sequence defined peptoids with diverse side-chains.. United States. https://doi.org/10.1016/bs.mie.2021.04.022
Connolly, Michael D, Xuan, Sunting, Molchanova, Natalia, and Zuckermann, Ronald N. 2021.
"Submonomer synthesis of sequence defined peptoids with diverse side-chains.". United States. https://doi.org/10.1016/bs.mie.2021.04.022. https://www.osti.gov/servlets/purl/1845665.
@article{osti_1845665,
title = {Submonomer synthesis of sequence defined peptoids with diverse side-chains.},
author = {Connolly, Michael D and Xuan, Sunting and Molchanova, Natalia and Zuckermann, Ronald N},
abstractNote = {Peptoids are a diverse family of sequence-defined oligomers of N-substituted glycine monomers, that can be readily accessed by the solid-phase submonomer synthesis method. Due to the versatility and efficiency of this chemistry, and the easy access to hundreds of potential monomers, there is an enormous potential sequence space that can be explored. This has enabled researchers from many different fields to custom-design peptoid sequences tailored to a wide variety of problems in biomedicine, nanoscience and polymer science. Here we provide detailed protocols for the synthesis of peptoids, using optimized protocols that can be performed by non-chemists. The submonomer method is fully compatible with Fmoc-peptide synthesis conditions, so the method is readily automated on existing automated peptide synthesizers using protocols provided here. Although the submonomer synthesis for peptoids is well established, there are special considerations required in order to access many of the most useful and desirable sidechains. Here we provide methods to include most of the amino-acid-like side chains, some of the most important non-natural monomer classes, as well as the creation of peptoid conjugates and peptide-peptoid hybrids.},
doi = {10.1016/bs.mie.2021.04.022},
url = {https://www.osti.gov/biblio/1845665},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Fri Jan 01 00:00:00 EST 2021},
month = {Fri Jan 01 00:00:00 EST 2021}
}
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