Carbodiimide-Mediated Beckmann Rearrangement of Oxyma-B as a Side Reaction in Peptide Synthesis

The suppression of side reactions is one of the most important objectives in peptide synthesis, where highly reactive compounds are involved. Recently, the violuric acid derivative Oxyma-B was introduced into peptide synthesis protocols as a promising additive to efficiently control the optical puri...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 13; p. 4235
Main Authors Orlandin, Andrea, Guryanov, Ivan, Ferrazzano, Lucia, Biondi, Barbara, Biscaglia, Francesca, Storti, Claudia, Rancan, Marzio, Formaggio, Fernando, Ricci, Antonio, Cabri, Walter
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 30.06.2022
MDPI
Subjects
amino acid
Amino acids
Beckman rearrangement
Carbodiimide
Carbon
coupling
Glucagon
Molecular weight
Optimization
Oxyma-B
peptide
Peptide synthesis
Peptides
Purity
racemization
Reagents
Side reactions
Spectrum analysis
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Summary:The suppression of side reactions is one of the most important objectives in peptide synthesis, where highly reactive compounds are involved. Recently, the violuric acid derivative Oxyma-B was introduced into peptide synthesis protocols as a promising additive to efficiently control the optical purity of the amino acids prone to racemization. However, we discovered a side reaction involving the Beckmann rearrangement of Oxyma-B during the coupling reaction, which compromises the yield and purity of the target peptides. Here, we present the investigation of the mechanism of this rearrangement and the optimization of the coupling reaction conditions to control it. These results can be taken into account for the design of novel efficient oxime-based coupling reagents.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27134235