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Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs)
Sugar amino acids (SAAs), as biologically interesting structures bearing both amino and carboxylic acid functional groups represent an important class of multifunctional building blocks. In this study, we develop an easy access to novel SAAs in only three steps starting from nitro compounds in high...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5919921/ https://www.ncbi.nlm.nih.gov/pubmed/29700416 http://dx.doi.org/10.1038/s41598-018-24927-6 |
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author | Tian, Guang-Zong Hu, Jing Zhang, Heng-Xi Rademacher, Christoph Zou, Xiao-Peng Zheng, Hong-Ning Xu, Fei Wang, Xiao-Li Linker, Torsten Yin, Jian |
author_facet | Tian, Guang-Zong Hu, Jing Zhang, Heng-Xi Rademacher, Christoph Zou, Xiao-Peng Zheng, Hong-Ning Xu, Fei Wang, Xiao-Li Linker, Torsten Yin, Jian |
author_sort | Tian, Guang-Zong |
collection | PubMed |
description | Sugar amino acids (SAAs), as biologically interesting structures bearing both amino and carboxylic acid functional groups represent an important class of multifunctional building blocks. In this study, we develop an easy access to novel SAAs in only three steps starting from nitro compounds in high yields in analytically pure form, easily available by ceric (IV) mediated radical additions. Such novel SAAs have been applied in the assembly of total nine carbopeptoids with the form of linear homo- and heterooligomers for the structural investigations employing circular dichroism (CD) spectroscopy, which suggest that the carbopeptoids emerge a well-extended, left (or right)-handed conformation similar to polyproline II (PPII) helices. NMR studies also clearly demonstrated the presence of ordered secondary structural elements. 2D-ROESY spectra were acquired to identify (i+1)NH ↔ (i)C(1)H, (i)C(2)H correlations which support the conformational analysis of tetramers by CD spectroscopy. These findings provide interesting information of SAAs and their oligomers as potential scaffolds for discovering new drugs and materials. |
format | Online Article Text |
id | pubmed-5919921 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-59199212018-05-01 Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) Tian, Guang-Zong Hu, Jing Zhang, Heng-Xi Rademacher, Christoph Zou, Xiao-Peng Zheng, Hong-Ning Xu, Fei Wang, Xiao-Li Linker, Torsten Yin, Jian Sci Rep Article Sugar amino acids (SAAs), as biologically interesting structures bearing both amino and carboxylic acid functional groups represent an important class of multifunctional building blocks. In this study, we develop an easy access to novel SAAs in only three steps starting from nitro compounds in high yields in analytically pure form, easily available by ceric (IV) mediated radical additions. Such novel SAAs have been applied in the assembly of total nine carbopeptoids with the form of linear homo- and heterooligomers for the structural investigations employing circular dichroism (CD) spectroscopy, which suggest that the carbopeptoids emerge a well-extended, left (or right)-handed conformation similar to polyproline II (PPII) helices. NMR studies also clearly demonstrated the presence of ordered secondary structural elements. 2D-ROESY spectra were acquired to identify (i+1)NH ↔ (i)C(1)H, (i)C(2)H correlations which support the conformational analysis of tetramers by CD spectroscopy. These findings provide interesting information of SAAs and their oligomers as potential scaffolds for discovering new drugs and materials. Nature Publishing Group UK 2018-04-26 /pmc/articles/PMC5919921/ /pubmed/29700416 http://dx.doi.org/10.1038/s41598-018-24927-6 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Tian, Guang-Zong Hu, Jing Zhang, Heng-Xi Rademacher, Christoph Zou, Xiao-Peng Zheng, Hong-Ning Xu, Fei Wang, Xiao-Li Linker, Torsten Yin, Jian Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) |
title | Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) |
title_full | Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) |
title_fullStr | Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) |
title_full_unstemmed | Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) |
title_short | Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs) |
title_sort | synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-c-branched sugar amino acids (saas) |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5919921/ https://www.ncbi.nlm.nih.gov/pubmed/29700416 http://dx.doi.org/10.1038/s41598-018-24927-6 |
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