312746-41-1Relevant articles and documents
Toward Enantiomerically Pure β-Seleno-α-amino Acids via Stereoselective Se-Michael Additions to Chiral Dehydroalanines
Oroz, Paula,Navo, Claudio D.,Avenoza, Alberto,Busto, Jesús H.,Corzana, Francisco,Jiménez-Osés, Gonzalo,Peregrina, Jesús M.
, p. 1955 - 1959 (2021)
The first totally chemo- and diastereoselective 1,4-conjugate additions of Se-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. The methodology is simple and does not require any catalyst, providing exceptional yields at room temperature, and involves the treatment of the corresponding diselenide compound with NaBH4 in the presence of the Dha. These Se-Michael additions provide an excellent channel for the synthesis of enantiomerically pure selenocysteine (Sec) derivatives, which pose high potential for chemical biology applications.
Synthesis of a selenocysteine-containing peptide by native chemical ligation
Gieselman, Matt D.,Xie, Lili,Van Der Donk, Wilfred A.
, p. 1331 - 1334 (2007/10/03)
(equation presented) A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.
