{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T14:34:36Z","timestamp":1790692476479,"version":"4.1.0"},"reference-count":34,"publisher":"Wiley","issue":"34","license":[{"start":{"date-parts":[[2023,7,13]],"date-time":"2023-07-13T00:00:00Z","timestamp":1689206400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100013994","name":"Nadace Experientia","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100013994","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001824","name":"Grantov\u00e1 Agentura \u010cesk\u00e9 Republiky","doi-asserted-by":"publisher","award":["GACR 22-07138O"],"award-info":[{"award-number":["GACR 22-07138O"]}],"id":[{"id":"10.13039\/501100001824","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004815","name":"Isaac Newton Trust","doi-asserted-by":"publisher","award":["22.39(l)"],"award-info":[{"award-number":["22.39(l)"]}],"id":[{"id":"10.13039\/501100004815","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2023,8,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Peptide stapling is a robust strategy for generating enzymatically stable, macrocyclic peptides. The incorporation of biologically relevant tags (such as cell\u2010penetrating motifs or fluorescent dyes) into peptides, while preserving their binding interactions and enhancing their stability, is highly sought after. Despite the unique opportunities offered by tryptophan\u2018s indole scaffold for targeted functionalisation, its utilisation in peptide stapling has been limited as compared to other amino acids. Herein, we present an approach for peptide stapling using the tryptophan\u2010mediated Petasis reaction. This method enables the synthesis of both stapled and labelled peptides and is applicable to both solution and solid\u2010phase synthesis. Importantly, the use of the Petasis reaction in combination with tryptophan facilitates the formation of stapled peptides in a straightforward, multicomponent fashion, while circumventing the formation of undesired by\u2010products. Furthermore, this approach allows for efficient and diverse late\u2010stage peptide modifications, thereby enabling rapid production of numerous conjugates for biological and medicinal applications.<\/jats:p>","DOI":"10.1002\/anie.202307782","type":"journal-article","created":{"date-parts":[[2023,6,30]],"date-time":"2023-06-30T16:13:36Z","timestamp":1688141616000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":34,"title":["Tryptophan in Multicomponent Petasis Reactions for Peptide Stapling and Late\u2010Stage Functionalisation"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0139-2360","authenticated-orcid":false,"given":"Sona","family":"Krajcovicova","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Cambridge  Lensfield road CB2\u20091EW Cambridge UK"},{"name":"Department of Organic Chemistry Palacky University Olomouc  Tr. 17. Listopadu 12 77900 Olomouc Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7355-2824","authenticated-orcid":false,"given":"David R.","family":"Spring","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Cambridge  Lensfield road CB2\u20091EW Cambridge UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,7,13]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/adtp.201800052"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24203654"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC00165E"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00532"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.9b00063"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.8b00906"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00126"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB00459A"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.7b00536"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC04022F"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508416"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608648"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc12010g"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201916257"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00744"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00214"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)02014-1"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b00024"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)61625-8"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812620"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC04697F"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC05934B"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611118"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8160"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202003548"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c03735"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03973"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02667F"},{"key":"e_1_2_8_29_1","unstructured":"Orthogonal deprotection conditions for Alloc would tolerate even highly acid-sensitive resins thus seemed to be most reliable."},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103271"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01747"},{"key":"e_1_2_8_32_1","unstructured":"3-(4-Boronophenyl)propanoic acid was used previously during testing of model substrates and it led to quantitative conversion. Also as mentioned above the use of glyoxylic acid would enable us further modified peptides after stapling thus we decided to focus on this option only."},{"key":"e_1_2_8_33_1","unstructured":"The yields were influenced by a loss during HPLC purification and not by incomplete conversion into the Petasis products."},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00522"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202307782","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,21]],"date-time":"2023-08-21T16:53:49Z","timestamp":1692636829000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202307782"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,13]]},"references-count":34,"journal-issue":{"issue":"34","published-print":{"date-parts":[[2023,8,21]]}},"alternative-id":["10.1002\/anie.202307782"],"URL":"https:\/\/doi.org\/10.1002\/anie.202307782","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,13]]},"assertion":[{"value":"2023-06-02","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-07-13","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202307782"}}