ArticleJournal of peptide science : an official publication of the European Peptide Society2015
Fmoc-Sec(Xan)-OH: synthesis and utility of Fmoc selenocysteine SPPS derivatives with acid-labile sidechain protection.
Article in Journal of peptide science : an official publication of the European Peptide Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 24 citations in OpenAlex.
- Simple Zn-Mediated Seleno- and Thio-Functionalization of Steroids at C-1 Position.International journal of molecular sciences · 2022Article
- Applying selenocysteine-mediated expressed protein ligation to prepare the membrane enzyme selenoprotein S.Methods in enzymology · 2022Article
- A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors.Molecules (Basel, Switzerland) · 2020Article
- Facile removal of 4-methoxybenzyl protecting group from selenocysteine.Journal of peptide science : an official publication of the European Peptide Society · 2019Article
- A "Seleno Effect" Differentiates the Roles of Redox Active Cysteine Residues in Plasmodium falciparum Thioredoxin Reductase.Biochemistry · 2018Article
- Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under "On Water" Conditions.Molecules (Basel, Switzerland) · 2017Article
- Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry.Molecules (Basel, Switzerland) · 2016Review
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Authors and funding
1 author at 1 institution in 1 country.
Funding
Abstract
We report here the synthesis of the first selenocysteine SPPS derivatives which bear TFA-labile sidechain protecting groups. New compounds Fmoc-Sec(Xan)-OH and Fmoc-Sec(Trt)-OH are presented as useful and practical alternatives to the traditional Fmoc-Sec-OH derivatives currently available to the peptide chemist. From a bis Fmoc-protected selenocystine precursor, multiple avenues of diselenide reduction were attempted to determine the most effective method for subsequent attachment of the protecting group electrophiles. Our previously reported one-pot reduction methodology was ultimately chosen as the optimal approach toward the synthesis of these novel building blocks, and both were easily obtained in high yield and purity. Fmoc-Sec(Xan)-OH was discovered to be bench-stable for extended timeframes while the corresponding Fmoc-Sec(Trt)-OH derivative appeared to detritylate slowly when not stored at -20 °C. Both Sec derivatives were incorporated into single- and multiple-Sec-containing test peptides in order to ascertain the peptides' deprotection behavior and final form upon TFA cleavage. Single-Sec-containing test peptides were always isolated as their corresponding diselenide dimers, while dual-Sec-containing peptide sequences were afforded exclusively as their intramolecular diselenides.
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Registered trials
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