Metal‐free sp 2 ‐C7−H Borylation of Tryptophan Containing Peptides and Late‐stage Modification
The discovery of milder and robust strategies to enable the introduction of organoboronates in peptides remains conspicuously underdeveloped. Herein, we demonstrate an efficient method for the site‐selective sp 2 ‐C7−H borylation of tryptophan under metal‐free condition using BBr 3 directed by pival...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2023-12, Vol.18 (23) |
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| container_title | Chemistry, an Asian journal |
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| creator | Meena, Rachana Shekhar, Shashank Ansari, Shabina B. Tiwari, Ashwani Lal, Jhajan Reddy, Damodara N. |
| description | The discovery of milder and robust strategies to enable the introduction of organoboronates in peptides remains conspicuously underdeveloped. Herein, we demonstrate an efficient method for the site‐selective
sp
2
‐C7−H borylation of tryptophan under metal‐free condition using BBr
3
directed by pivaloyl group. The versatility of this approach is that gram scale synthesis and C7‐borylated
N
‐Phth‐Trp(
N
‐Piv)(C7‐BPin)‐OMe was modified into various C7‐substituted derivatives. Moreover, the strategy enables for the peptide elongation and late‐stage borylation of peptides, natural product Brevianamide F and drug Oglufanide. |
| doi_str_mv | 10.1002/asia.202300638 |
| format | Article |
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sp
2
‐C7−H borylation of tryptophan under metal‐free condition using BBr
3
directed by pivaloyl group. The versatility of this approach is that gram scale synthesis and C7‐borylated
N
‐Phth‐Trp(
N
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sp
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directed by pivaloyl group. The versatility of this approach is that gram scale synthesis and C7‐borylated
N
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sp
2
‐C7−H borylation of tryptophan under metal‐free condition using BBr
3
directed by pivaloyl group. The versatility of this approach is that gram scale synthesis and C7‐borylated
N
‐Phth‐Trp(
N
‐Piv)(C7‐BPin)‐OMe was modified into various C7‐substituted derivatives. Moreover, the strategy enables for the peptide elongation and late‐stage borylation of peptides, natural product Brevianamide F and drug Oglufanide.</abstract><doi>10.1002/asia.202300638</doi><orcidid>https://orcid.org/0000-0001-9762-9160</orcidid></addata></record> |
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| identifier | ISSN: 1861-4728 |
| ispartof | Chemistry, an Asian journal, 2023-12, Vol.18 (23) |
| issn | 1861-4728 1861-471X |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_asia_202300638 |
| source | Wiley Online Library Journals Frontfile Complete |
| title | Metal‐free sp 2 ‐C7−H Borylation of Tryptophan Containing Peptides and Late‐stage Modification |
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