A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent
1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz), a readily available and bench stable benziodoxole-based iodine(III) reagent, can be employed for the synthesis of dipeptides from various standard and sterically hindered amino acids in the presence of (4-MeOC6H4)3P. The combined system of IBA-OBz/(...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2020-03-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00183/full |
| _version_ | 1819152587933351936 |
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| author | Li-Jun Qiu Dan Liu Ke Zheng Ming-Tao Zhang Chi Zhang |
| author_facet | Li-Jun Qiu Dan Liu Ke Zheng Ming-Tao Zhang Chi Zhang |
| author_sort | Li-Jun Qiu |
| collection | DOAJ |
| description | 1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz), a readily available and bench stable benziodoxole-based iodine(III) reagent, can be employed for the synthesis of dipeptides from various standard and sterically hindered amino acids in the presence of (4-MeOC6H4)3P. The combined system of IBA-OBz/(4-MeOC6H4)3P is also successfully applied to the solid-phase peptide synthesis and a pentapeptide leu-enkephalin in unprotected form has been synthesized. Density functional theory calculations reveal that the rate-limiting step is nucleophilic attack of 4-dimethylaminopyridine (DMAP) onto IBA-OBz. |
| first_indexed | 2024-12-22T14:51:40Z |
| format | Article |
| id | doaj.art-faee0fde2c3e4c79ac4eeeec54300883 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-22T14:51:40Z |
| publishDate | 2020-03-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-faee0fde2c3e4c79ac4eeeec543008832022-12-21T18:22:18ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-03-01810.3389/fchem.2020.00183526026A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling ReagentLi-Jun Qiu0Dan Liu1Ke Zheng2Ming-Tao Zhang3Chi Zhang4State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, ChinaState Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, ChinaState Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, ChinaComputational Center for Molecular Science, Nankai University, Tianjin, ChinaState Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz), a readily available and bench stable benziodoxole-based iodine(III) reagent, can be employed for the synthesis of dipeptides from various standard and sterically hindered amino acids in the presence of (4-MeOC6H4)3P. The combined system of IBA-OBz/(4-MeOC6H4)3P is also successfully applied to the solid-phase peptide synthesis and a pentapeptide leu-enkephalin in unprotected form has been synthesized. Density functional theory calculations reveal that the rate-limiting step is nucleophilic attack of 4-dimethylaminopyridine (DMAP) onto IBA-OBz.https://www.frontiersin.org/article/10.3389/fchem.2020.00183/fullpeptideIBA-OBzhypervalent iodine(III) reagentsolid-phase peptide synthesis (SPPS)DFT calculations |
| spellingShingle | Li-Jun Qiu Dan Liu Ke Zheng Ming-Tao Zhang Chi Zhang A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent Frontiers in Chemistry peptide IBA-OBz hypervalent iodine(III) reagent solid-phase peptide synthesis (SPPS) DFT calculations |
| title | A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent |
| title_full | A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent |
| title_fullStr | A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent |
| title_full_unstemmed | A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent |
| title_short | A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent |
| title_sort | benziodoxole based hypervalent iodine iii compound functioning as a peptide coupling reagent |
| topic | peptide IBA-OBz hypervalent iodine(III) reagent solid-phase peptide synthesis (SPPS) DFT calculations |
| url | https://www.frontiersin.org/article/10.3389/fchem.2020.00183/full |
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