Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles
Our recently discovered, selective, on-resin route to N(τ)-alkylated imidazolium-containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as...
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| Format: | Article |
| Language: | en_US |
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Wiley Blackwell
2016
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| Online Access: | http://hdl.handle.net/1721.1/105840 https://orcid.org/0000-0002-9547-3251 |
| _version_ | 1811085957699469312 |
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| author | Qian, Wen-Jian Park, Jung-Eun Lai, Christopher C. Kelley, James A. Lee, Kyung S. Burke, Terrence R. Grant, Robert A Yaffe, Michael B |
| author2 | Massachusetts Institute of Technology. Department of Biological Engineering |
| author_facet | Massachusetts Institute of Technology. Department of Biological Engineering Qian, Wen-Jian Park, Jung-Eun Lai, Christopher C. Kelley, James A. Lee, Kyung S. Burke, Terrence R. Grant, Robert A Yaffe, Michael B |
| author_sort | Qian, Wen-Jian |
| collection | MIT |
| description | Our recently discovered, selective, on-resin route to N(τ)-alkylated imidazolium-containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring-forming junctions. Interestingly, these cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts. |
| first_indexed | 2024-09-23T13:18:31Z |
| format | Article |
| id | mit-1721.1/105840 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:18:31Z |
| publishDate | 2016 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/1058402022-09-28T13:19:44Z Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles Qian, Wen-Jian Park, Jung-Eun Lai, Christopher C. Kelley, James A. Lee, Kyung S. Burke, Terrence R. Grant, Robert A Yaffe, Michael B Massachusetts Institute of Technology. Department of Biological Engineering Massachusetts Institute of Technology. Department of Biology Grant, Robert A Yaffe, Michael B Our recently discovered, selective, on-resin route to N(τ)-alkylated imidazolium-containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring-forming junctions. Interestingly, these cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts. National Institutes of Health (U.S.) (Grants ES015339 and GM104047) 2016-12-15T20:49:55Z 2016-12-15T20:49:55Z 2015-11 2015-06 Article http://purl.org/eprint/type/JournalArticle 1097-0282 0006-3525 http://hdl.handle.net/1721.1/105840 Qian, Wen-Jian et al. “Neighbor-Directed Histidine N (τ)-Alkylation: A Route to Imidazolium-Containing Phosphopeptide Macrocycles: Neighbor-Directed Histidine N(τ)-Alkylation.” Biopolymers 104.6 (2015): 663–673. https://orcid.org/0000-0002-9547-3251 en_US http://dx.doi.org/10.1002/bip.22698 Biopolymers Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf Wiley Blackwell PMC |
| spellingShingle | Qian, Wen-Jian Park, Jung-Eun Lai, Christopher C. Kelley, James A. Lee, Kyung S. Burke, Terrence R. Grant, Robert A Yaffe, Michael B Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
| title | Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
| title_full | Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
| title_fullStr | Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
| title_full_unstemmed | Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
| title_short | Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
| title_sort | neighbor directed histidine n τ alkylation a route to imidazolium containing phosphopeptide macrocycles |
| url | http://hdl.handle.net/1721.1/105840 https://orcid.org/0000-0002-9547-3251 |
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