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This methodology is grounded on the incorporation of N-(cyanoethyl)prolyl residue followed by on-site oxidation by Cope elimination with m-chloroperbenzoic acid, exploring the unrecognized dual role of the cyanoethyl group as an effective N-protecting group under peptide synthesis conditions and as a suitable leaving group during the chemoselective on-site N-oxidation. Following this protocol N-hydroxy-MIF-1 is obtained in 78% global yield from N-(cyanoethyl)-l-proline. This synthetic approach opens a new avenue for access to N-hydroxylated Melanostatin analogues with direct application in neurochemistry and Parkinson\u2019s research.<\/jats:p>","DOI":"10.1055\/a-1695-1095","type":"journal-article","created":{"date-parts":[[2021,11,12]],"date-time":"2021-11-12T00:03:12Z","timestamp":1636675392000},"page":"2031-2036","source":"Crossref","is-referenced-by-count":5,"title":["A Convenient On-Site Oxidation Strategy for the N-Hydroxylation of Melanostatin Neuropeptide Using Cope Elimination"],"prefix":"10.1055","volume":"54","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9071-6197","authenticated-orcid":false,"given":"Ivo E.","family":"Sampaio-Dias","sequence":"first","affiliation":[]},{"given":"Sara C.","family":"Silva-Reis","sequence":"additional","affiliation":[]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1464-7254","authenticated-orcid":false,"given":"Beatriz L.","family":"Pires-Lima","sequence":"additional","affiliation":[]},{"given":"Xavier Cruz","family":"Correia","sequence":"additional","affiliation":[]},{"given":"Hugo F.","family":"Costa-Almeida","sequence":"additional","affiliation":[]}],"member":"194","published-online":{"date-parts":[[2022,2,2]]},"reference":[{"key":"ref1","doi-asserted-by":"crossref","first-page":"3690","DOI":"10.1039\/D0OB00664E","volume":"18","author":"M P Sarnowski","year":"2020","journal-title":"Org. 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