- 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+1NH <-> (C1H)-C-i, (C2H)-C-i correlations which support the conformational analysis of tetramers by CD spectroscopy. These findings provide interesting information of SAAsSugar 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+1NH <-> (C1H)-C-i, (C2H)-C-i 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.…
MetadatenAuthor details: | Guang-Zong Tian, Jing Hu, Heng-Xi Zhang, Christoph RademacherORCiD, Xiao-Peng Zou, Hong-Ning Zheng, Fei Xu, Xiao-Li Wang, Torsten LinkerORCiDGND, Jian Yin |
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DOI: | https://doi.org/10.1038/s41598-018-24927-6 |
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ISSN: | 2045-2322 |
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Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/29700416 |
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Title of parent work (English): | Scientific reports |
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Publisher: | Nature Publ. Group |
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Place of publishing: | London |
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Publication type: | Article |
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Language: | English |
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Date of first publication: | 2018/04/26 |
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Publication year: | 2018 |
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Release date: | 2021/12/08 |
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Volume: | 8 |
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Number of pages: | 8 |
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Funding institution: | National Natural Science Foundation of ChinaNational Natural Science Foundation of China [21302068, 21502071]; Natural Science Foundation of Jiangsu ProvinceJiangsu Planned Projects for Postdoctoral Research FundsNatural Science Foundation of Jiangsu Province [BK20150154]; Fundamental Research Funds for the Central UniversitiesFundamental Research Funds for the Central Universities [JUSRP51712B]; Public Health Research Center at Jiangnan University [JUPH201502]; Max Planck Society International Partner Group Program; High-end Foreign Experts Recruitment Program; Thousand Talents Plan (Young Professionals); China Scholarship CouncilChina Scholarship Council |
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Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
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DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
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License (German): | CC-BY - Namensnennung 4.0 International |
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