Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility
This article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase pe...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.250 |
| _version_ | 1831678905561382912 |
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| author | Dan Yuan Xuewen Du Junfeng Shi Ning Zhou Abdulgader Ahmed Baoum Bing Xu |
| author_facet | Dan Yuan Xuewen Du Junfeng Shi Ning Zhou Abdulgader Ahmed Baoum Bing Xu |
| author_sort | Dan Yuan |
| collection | DOAJ |
| description | This article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase peptide synthesis (SPPS) to build the peptide segment (Phe-Arg-Gly-Asp or naphthAla-Phe-Arg-Gly-Asp with fully protected groups), and later, an amidation reaction in liquid phase connects these three parts together. The overall yield of these multiple step synthesis is about 34%. Besides exhibiting excellent solubility, these conjugates of saccharide–amino acids–nucleobase (SAN), like the previously reported conjugates of nucleobase–amino acids–saccharide (NAS) and nucleobase–saccharide–amino acids (NSA), are mammalian cell compatible. |
| first_indexed | 2024-12-20T05:08:15Z |
| format | Article |
| id | doaj.art-de5af19700f845f6a3577ba73d3f0482 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T05:08:15Z |
| publishDate | 2014-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-de5af19700f845f6a3577ba73d3f04822022-12-21T19:52:19ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-10-011012406241310.3762/bjoc.10.2501860-5397-10-250Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibilityDan Yuan0Xuewen Du1Junfeng Shi2Ning Zhou3Abdulgader Ahmed Baoum4Bing Xu5Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USADepartment of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USADepartment of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USADepartment of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USADepartment of Chemistry, King Abdulaziz University, Jeddah, Saudi ArabiaDepartment of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USAThis article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase peptide synthesis (SPPS) to build the peptide segment (Phe-Arg-Gly-Asp or naphthAla-Phe-Arg-Gly-Asp with fully protected groups), and later, an amidation reaction in liquid phase connects these three parts together. The overall yield of these multiple step synthesis is about 34%. Besides exhibiting excellent solubility, these conjugates of saccharide–amino acids–nucleobase (SAN), like the previously reported conjugates of nucleobase–amino acids–saccharide (NAS) and nucleobase–saccharide–amino acids (NSA), are mammalian cell compatible.https://doi.org/10.3762/bjoc.10.250cell compatibilitynucleobasepeptidessaccharide |
| spellingShingle | Dan Yuan Xuewen Du Junfeng Shi Ning Zhou Abdulgader Ahmed Baoum Bing Xu Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility Beilstein Journal of Organic Chemistry cell compatibility nucleobase peptides saccharide |
| title | Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility |
| title_full | Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility |
| title_fullStr | Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility |
| title_full_unstemmed | Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility |
| title_short | Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility |
| title_sort | synthesis of novel conjugates of a saccharide amino acids nucleobase and the evaluation of their cell compatibility |
| topic | cell compatibility nucleobase peptides saccharide |
| url | https://doi.org/10.3762/bjoc.10.250 |
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