Bibliographic Details
| Title: |
A Convenient On-Site Oxidation Strategy for the N -Hydroxylation of Melanostatin Neuropeptide Using Cope Elimination. |
| Authors: |
Sampaio-Dias, Ivo E., Silva-Reis, Sara C., Pires-Lima, Beatriz L., Correia, Xavier Cruz, Costa-Almeida, Hugo F. |
| Source: |
Synthesis; Apr2022, Vol. 54 Issue 8, p2031-2036, 6p |
| Subject Terms: |
PARKINSON'S disease, PEPTIDE synthesis, PSYCHOLOGICAL adaptation, NEUROCHEMISTRY, PROLINE |
| Abstract: |
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)- l -proline. This synthetic approach opens a new avenue for access to N -hydroxylated Melanostatin analogues with direct application in neurochemistry and Parkinson's research. [ABSTRACT FROM AUTHOR] |
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| Database: |
Complementary Index |
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