Synthesis of selenocysteine and selenomethionine derivatives from sulfur-containing amino acids.
Selenium-containing amino acids have attracted increasing interest from view points of the importance as active centers of several selenoenzymes, the biological synthesis, the metabolism, and the use for structure determination of proteins. In this article, our recent progresses in the transformation from sulfur-containing amino acids to selenocysteine (SeCys) and selenomethionine (SeMet) derivatives are reviewed along with the surveys of general organic methodologies for the synthesis of SeCys and SeMet derivatives in the literature. The S-->Se modification (i.e., the chemical atomic mutation) would be a useful approach to peptide synthesis involving selenoamino acid residues.
Iwaoka
Michio
M
Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292, Japan. miwaoka@tokai.ac.jp
Ooka
Ryuta
R
Nakazato
Toshifumi
T
Yoshida
Sari
S
Oishi
Sadahiro
S
D003545:Cysteine / Q000737:chemistry*; D008715:Methionine / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D017279:Selenocysteine / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000378:metabolism; D012645:Selenomethionine / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
D010455:Peptides; D017279:Selenocysteine; D012645:Selenomethionine; D008715:Methionine; D003545:Cysteine