Insights into the deselenization of selenocysteine into alanine and serine

The development of native chemical ligation coupled with desulfurization has allowed ligation at several new ligation junctions. However, desulfurization also converts all cysteine residues in the protein sequence into alanine. Deselenization of selenocysteine, in contrast, selectively removes the s...

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Published inChemical science (Cambridge) Vol. 6; no. 11; pp. 6207 - 6212
Main Authors Dery, Shahar, Reddy, Post Sai, Dery, Linoy, Mousa, Reem, Dardashti, Rebecca Notis, Metanis, Norman
Format Journal Article
LanguageEnglish
Published England 01.11.2015
Subjects
Alanine
Anaerobic conditions
Cysteine
Desulfurizing
Joining
Oxygen content
Residues
Saturation
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Summary:The development of native chemical ligation coupled with desulfurization has allowed ligation at several new ligation junctions. However, desulfurization also converts all cysteine residues in the protein sequence into alanine. Deselenization of selenocysteine, in contrast, selectively removes the selenol group to give alanine in the presence of unprotected cysteines. In this study we shed more light onto the deselenization mechanism of selenocysteine to alanine and provide optimized conditions for the reaction. The deselenization can be accomplished in one minute under anaerobic conditions to give alanine. Under aerobic conditions (oxygen saturation), selenocysteine is converted into serine.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc02528a