Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions
A practical procedure for [superscript 11]CN-labeling of unprotected peptides has been developed. The method was shown to be highly chemoselective for cysteine over other potentially nucleophilic residues, and the radiolabeled products were synthesized and purified in less than 15 min. Appropriate f...
| Main Authors: | , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society (ACS)
2020
|
| Online Access: | https://hdl.handle.net/1721.1/126030 |
| _version_ | 1826199102035066880 |
|---|---|
| author | Zhao, Wenjun Lee, Hong Geun Buchwald, Stephen Leffler Hooker, Jacob M. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Zhao, Wenjun Lee, Hong Geun Buchwald, Stephen Leffler Hooker, Jacob M. |
| author_sort | Zhao, Wenjun |
| collection | MIT |
| description | A practical procedure for [superscript 11]CN-labeling of unprotected peptides has been developed. The method was shown to be highly chemoselective for cysteine over other potentially nucleophilic residues, and the radiolabeled products were synthesized and purified in less than 15 min. Appropriate for biomedical applications, the method could be used on an extremely small scale (20 nmol) with a high radiochemical yield. The success of the protocol stems from the use of a Pd-reagent based on a dihaloarene, which enables direct “nucleophile-nucleophile” coupling of the peptide and [superscript 11]C cyanide by temporal separation of nucleophile addition. |
| first_indexed | 2024-09-23T11:14:45Z |
| format | Article |
| id | mit-1721.1/126030 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T11:14:45Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1260302022-10-01T02:20:07Z Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions Direct [superscript 11]CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions Zhao, Wenjun Lee, Hong Geun Buchwald, Stephen Leffler Hooker, Jacob M. Massachusetts Institute of Technology. Department of Chemistry A practical procedure for [superscript 11]CN-labeling of unprotected peptides has been developed. The method was shown to be highly chemoselective for cysteine over other potentially nucleophilic residues, and the radiolabeled products were synthesized and purified in less than 15 min. Appropriate for biomedical applications, the method could be used on an extremely small scale (20 nmol) with a high radiochemical yield. The success of the protocol stems from the use of a Pd-reagent based on a dihaloarene, which enables direct “nucleophile-nucleophile” coupling of the peptide and [superscript 11]C cyanide by temporal separation of nucleophile addition. NIH (grant no. R01GM46059) Department of Energy (grant no. DE-SC0008430) National Center for Research Resources (grant no. P41RR14075) 2020-06-30T20:55:06Z 2020-06-30T20:55:06Z 2017-05 2019-12-12T18:19:41Z Article http://purl.org/eprint/type/JournalArticle 1520-5126 https://hdl.handle.net/1721.1/126030 Zhao, Wenjun, et al., "Direct 11 CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions." Journal of the American Chemical Society 139, 21 (2017): p. 7152-55 doi 10.1021/JACS.7B02761 ©2017 Author(s) en 10.1021/JACS.7B02761 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Zhao, Wenjun Lee, Hong Geun Buchwald, Stephen Leffler Hooker, Jacob M. Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions |
| title | Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions |
| title_full | Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions |
| title_fullStr | Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions |
| title_full_unstemmed | Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions |
| title_short | Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions |
| title_sort | direct 11cn labeling of unprotected peptides via palladium mediated sequential cross coupling reactions |
| url | https://hdl.handle.net/1721.1/126030 |
| work_keys_str_mv | AT zhaowenjun direct11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT leehonggeun direct11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT buchwaldstephenleffler direct11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT hookerjacobm direct11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT zhaowenjun directsuperscript11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT leehonggeun directsuperscript11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT buchwaldstephenleffler directsuperscript11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions AT hookerjacobm directsuperscript11cnlabelingofunprotectedpeptidesviapalladiummediatedsequentialcrosscouplingreactions |