36901-98-1Relevant academic research and scientific papers
A Convenient On-Site Oxidation Strategy for the N -Hydroxylation of Melanostatin Neuropeptide Using Cope Elimination
Correia, Xavier Cruz,Costa-Almeida, Hugo F.,Pires-Lima, Beatriz L.,Sampaio-Dias, Ivo E.,Silva-Reis, Sara C.
, (2022/02/16)
A convenient synthetic protocol for the unprecedented N-hydroxylation of proline residue in Melanostatin (MIF-1) neuropeptide is reported. 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)-Lproline. This synthetic approach opens a new avenue for access to N-hydroxylated Melanostatin analogues with direct application in neurochemistry and Parkinson s research.
The synthesis of functionalised chiral bicyclic lactam and lactone N-oxides using a tandem Cope elimination/reverse Cope elimination protocol
Ellis, Gemma L.,O'Neil, Ian A.,Elena Ramos,Cleator, Ed,Barret Kalindjian,Chorlton, Alan P.,Tapolczay, David J.
, p. 1683 - 1686 (2008/02/05)
Functionalised hydroxylamine derivatives of (S)-proline and (R)-pipecolic acid have been prepared using a Cope elimination. These undergo reverse Cope elimination onto a pendant double bond to give bicyclic lactam and lactone N-oxides containing three contiguous chiral centres, this extends the scope and applicability of the reverse Cope elimination in the synthesis of heterocyclic systems by incorporation of the lactone and lactam structural motifs.
