N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis
Peptide coupling with minimal protection is one of the desired methods for the synthesis of peptides and proteins. To achieve regioselective amide bond formation, side chain protection is often essential; however, protecting groups potentially diminish peptide solubility and render the polar polyami...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2019-03-01
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| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00173/full |
| _version_ | 1811300694113648640 |
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| author | Ryo Okamoto Emiko Ono Masayuki Izumi Yasuhiro Kajihara |
| author_facet | Ryo Okamoto Emiko Ono Masayuki Izumi Yasuhiro Kajihara |
| author_sort | Ryo Okamoto |
| collection | DOAJ |
| description | Peptide coupling with minimal protection is one of the desired methods for the synthesis of peptides and proteins. To achieve regioselective amide bond formation, side chain protection is often essential; however, protecting groups potentially diminish peptide solubility and render the polar polyamide chain amphipathic due to their apolar nature. In this manuscript, we describe a new protecting group, N,N-dimethylaminoxy carbonyl (Dmaoc), and its use in peptide coupling reactions. The Dmaoc group has a relatively polar character compared to the Boc group, which is a conventional protecting group for the Nε-amine of Lys residues. This polar protecting group is removable by reduction in the buffer containing (±)-dithiothreitol (DTT). Furthermore, the Dmaoc group proved compatible with peptide ligation strategies featuring the activation of N-acyl diaminobenzamides (Dbz) with sodium nitrate to generate the respective benzotriazole leaving group. The Dmaoc/Dbz strategy described in this manuscript provides a new method for the chemical synthesis of peptides. |
| first_indexed | 2024-04-13T06:56:09Z |
| format | Article |
| id | doaj.art-9c588cb558f2479faf18a5224ab776a4 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-13T06:56:09Z |
| publishDate | 2019-03-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-9c588cb558f2479faf18a5224ab776a42022-12-22T02:57:15ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-03-01710.3389/fchem.2019.00173447053N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide SynthesisRyo OkamotoEmiko OnoMasayuki IzumiYasuhiro KajiharaPeptide coupling with minimal protection is one of the desired methods for the synthesis of peptides and proteins. To achieve regioselective amide bond formation, side chain protection is often essential; however, protecting groups potentially diminish peptide solubility and render the polar polyamide chain amphipathic due to their apolar nature. In this manuscript, we describe a new protecting group, N,N-dimethylaminoxy carbonyl (Dmaoc), and its use in peptide coupling reactions. The Dmaoc group has a relatively polar character compared to the Boc group, which is a conventional protecting group for the Nε-amine of Lys residues. This polar protecting group is removable by reduction in the buffer containing (±)-dithiothreitol (DTT). Furthermore, the Dmaoc group proved compatible with peptide ligation strategies featuring the activation of N-acyl diaminobenzamides (Dbz) with sodium nitrate to generate the respective benzotriazole leaving group. The Dmaoc/Dbz strategy described in this manuscript provides a new method for the chemical synthesis of peptides.https://www.frontiersin.org/article/10.3389/fchem.2019.00173/fullN,N-dimethylaminoxy carbonylDmaocDbzpeptide couplingsolid phase peptide synthesischemical ligation |
| spellingShingle | Ryo Okamoto Emiko Ono Masayuki Izumi Yasuhiro Kajihara N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis Frontiers in Chemistry N,N-dimethylaminoxy carbonyl Dmaoc Dbz peptide coupling solid phase peptide synthesis chemical ligation |
| title | N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis |
| title_full | N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis |
| title_fullStr | N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis |
| title_full_unstemmed | N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis |
| title_short | N,N-Dimethylaminoxy Carbonyl, a Polar Protecting Group for Efficient Peptide Synthesis |
| title_sort | n n dimethylaminoxy carbonyl a polar protecting group for efficient peptide synthesis |
| topic | N,N-dimethylaminoxy carbonyl Dmaoc Dbz peptide coupling solid phase peptide synthesis chemical ligation |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00173/full |
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