Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers

[Image: see text] We report the fluorenylmethoxycarbonyl (Fmoc) protection of functionalized bis-amino acid building blocks using a temporary Cu(2+) complexation strategy, together with an efficient multikilogram-scale synthesis of bis-amino acid precursors. This allows the synthesis of stereochemic...

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Autores principales: Xie, Yihui, Luo, Danni, Wiener, Jesse, Tang, Sicheng, Chepyshev, Sergiy, Schafmeister, Christian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9113113/
https://www.ncbi.nlm.nih.gov/pubmed/35499925
http://dx.doi.org/10.1021/acs.orglett.2c01295
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author Xie, Yihui
Luo, Danni
Wiener, Jesse
Tang, Sicheng
Chepyshev, Sergiy
Schafmeister, Christian
author_facet Xie, Yihui
Luo, Danni
Wiener, Jesse
Tang, Sicheng
Chepyshev, Sergiy
Schafmeister, Christian
author_sort Xie, Yihui
collection PubMed
description [Image: see text] We report the fluorenylmethoxycarbonyl (Fmoc) protection of functionalized bis-amino acid building blocks using a temporary Cu(2+) complexation strategy, together with an efficient multikilogram-scale synthesis of bis-amino acid precursors. This allows the synthesis of stereochemically and functionally diverse spiroligomers utilizing solid-phase Fmoc/tBu chemistry to facilitate the development of applications. Four tetramers were assembled on a semiautomated microwave peptide synthesizer. We determined their secondary structures with two-dimensional nuclear magnetic resonance spectroscopy.
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spelling pubmed-91131132023-05-02 Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers Xie, Yihui Luo, Danni Wiener, Jesse Tang, Sicheng Chepyshev, Sergiy Schafmeister, Christian Org Lett [Image: see text] We report the fluorenylmethoxycarbonyl (Fmoc) protection of functionalized bis-amino acid building blocks using a temporary Cu(2+) complexation strategy, together with an efficient multikilogram-scale synthesis of bis-amino acid precursors. This allows the synthesis of stereochemically and functionally diverse spiroligomers utilizing solid-phase Fmoc/tBu chemistry to facilitate the development of applications. Four tetramers were assembled on a semiautomated microwave peptide synthesizer. We determined their secondary structures with two-dimensional nuclear magnetic resonance spectroscopy. American Chemical Society 2022-05-02 2022-05-13 /pmc/articles/PMC9113113/ /pubmed/35499925 http://dx.doi.org/10.1021/acs.orglett.2c01295 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Xie, Yihui
Luo, Danni
Wiener, Jesse
Tang, Sicheng
Chepyshev, Sergiy
Schafmeister, Christian
Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers
title Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers
title_full Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers
title_fullStr Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers
title_full_unstemmed Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers
title_short Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers
title_sort development of fmoc-protected bis-amino acids toward automated synthesis of highly functionalized spiroligomers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9113113/
https://www.ncbi.nlm.nih.gov/pubmed/35499925
http://dx.doi.org/10.1021/acs.orglett.2c01295
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