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Nitrogen arylation for macrocyclization of unprotected peptides
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lautrette, Guillaume | - |
dc.contributor.author | Touti, Faycal | - |
dc.contributor.author | Lee, Hong Geun | - |
dc.contributor.author | Dai, Peng | - |
dc.contributor.author | Pentelute, Bradley L. | - |
dc.creator | 이홍근 | - |
dc.date.accessioned | 2019-04-24T08:31:13Z | - |
dc.date.available | 2020-04-05T08:31:13Z | - |
dc.date.created | 2018-10-29 | - |
dc.date.issued | 2016-07 | - |
dc.identifier.citation | Journal of the American Chemical Society, Vol.138 No.27, pp.8340-8343 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://hdl.handle.net/10371/148008 | - |
dc.description.abstract | We describe an efficient and mild method for the synthesis of macrocyclic peptides-via nitrogen arylation from unprotected precursors. Various electrophiles and lysine-based nucleophiles were investigated and showed high-yielding product formation, even for a macrocyclization scan with 14 variants. We found that nitrogen-linked aryl products were more stable to base and oxidation when compared to thiol arylated species, thereby highlighting the utility of this methodology. Finally, N-aryl macrocyclization was performed on a p53 peptide inhibitor of MDM2 and resulted in identification of a nanomolar binder with improved proteolytic stability and cell permeability. | - |
dc.language | 영어 | - |
dc.language.iso | en | en |
dc.publisher | American Chemical Society | - |
dc.title | Nitrogen arylation for macrocyclization of unprotected peptides | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/jacs.6b03757 | - |
dc.citation.journaltitle | Journal of the American Chemical Society | - |
dc.identifier.wosid | 000379794400006 | - |
dc.identifier.scopusid | 2-s2.0-84978747042 | - |
dc.description.srnd | OAIID:RECH_ACHV_DSTSH_NO:T201720251 | - |
dc.description.srnd | RECH_ACHV_FG:RR00200001 | - |
dc.description.srnd | ADJUST_YN: | - |
dc.description.srnd | EMP_ID:A080564 | - |
dc.description.srnd | CITE_RATE:13.858 | - |
dc.description.srnd | FILENAME:3. jacs.6b03757.pdf | - |
dc.description.srnd | DEPT_NM:화학부 | - |
dc.description.srnd | EMAIL:hgleee@snu.ac.kr | - |
dc.description.srnd | SCOPUS_YN:Y | - |
dc.description.srnd | FILEURL:https://srnd.snu.ac.kr/eXrepEIR/fws/file/8321a9bd-769a-4ee4-ab07-433762d713be/link | - |
dc.citation.endpage | 8343 | - |
dc.citation.number | 27 | - |
dc.citation.startpage | 8340 | - |
dc.citation.volume | 138 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Lee, Hong Geun | - |
dc.identifier.srnd | T201720251 | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | CROSS-COUPLING REACTIONS | - |
dc.subject.keywordPlus | STAPLED PEPTIDES | - |
dc.subject.keywordPlus | ARYL HALIDES | - |
dc.subject.keywordPlus | BH3 HELIX | - |
dc.subject.keywordPlus | IN-VIVO | - |
dc.subject.keywordPlus | PALLADIUM | - |
dc.subject.keywordPlus | CONJUGATION | - |
dc.subject.keywordPlus | INHIBITION | - |
dc.subject.keywordPlus | ACTIVATION | - |
dc.subject.keywordPlus | STABILITY | - |
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