Synthetic simulation of nonribosomal peptide biosynthesis. A dual role of alkylthiol esters in peptide synthesis

1976 ◽  
Vol 32 (8) ◽  
pp. 967-968 ◽  
Author(s):  
S. Yamada ◽  
Y. Yokoyama ◽  
T. Shioiri
Keyword(s):  
Peptide Synthesis ◽  
Dual Role ◽  
Nonribosomal Peptide ◽  
Peptide Biosynthesis ◽  
Synthetic Simulation

A Convenient On-Site Oxidation Strategy for the N-hydroxylation of Melanostatin Neuropeptide using Cope Elimination

Synthesis ◽  
2021 ◽  
Author(s):  
Ivo Dias ◽  
Sara C. Silva-Reis ◽  
Beatriz L. Pires-Lima ◽  
Xavier C. Correia ◽  
Hugo F. Costa-Almeida
Keyword(s):  
Peptide Synthesis ◽  
Dual Role ◽  
Direct Application ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Proline Residue ◽  
Synthesis Conditions ◽  
Leaving Group ◽  
Cyanoethyl Group

In this work, 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 with 78% global yield from N-(cyanoethyl)-L-proline. This synthetic approach opens a new avenue for access to N-hydroxylated Melanostatin analogs with direct application in neurochemistry and Parkinson’s research.

Dual role of B7 costimulation in obesity-related non-alcoholic steatohepatitis (NASH) and metabolic dysregulation

2014 ◽  
Vol 122 (03) ◽  
Author(s):  
A Chatzigeorgiou ◽  
R Garcia-Martin ◽  
KJ Chung ◽  
I Alexaki ◽  
A Klotzsche-von Ameln ◽  
...  
Keyword(s):  
Dual Role ◽  
Alcoholic Steatohepatitis ◽  
Metabolic Dysregulation

A dual role of the N-terminal FQQI motif in GLUT4 trafficking

2008 ◽  
Vol 3 (S 1) ◽  
Author(s):  
U Bernhardt ◽  
HG Joost ◽  
H Al-Hasani
Keyword(s):  
Dual Role

Dual Role of RKIP in NF-kB Signaling Pathways

2011 ◽  
Vol 2 (1) ◽  
pp. 21-34
Author(s):  
Huihui Tang ◽  
Sungdae Park ◽  
Kam C. Yeung
Keyword(s):  
Signaling Pathways ◽  
Dual Role
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