title: Enantioselective synthesis of alpha-methyl-D-cysteine and lanthionine building blocks via alpha-methyl-D-serine-beta-lactone.
abstract: [reaction: see text] We report here the enantioselective synthesis of Boc-alpha-methyl-d-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-alpha-methyl-d-serine-beta-lactone.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0343, USA.
authors.forename: Nicole D
authors.initials: ND
authors.lastname: Smith
authors.forename: Murray
authors.initials: M
authors.lastname: Goodman
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013440:Sulfides
chemical_list: D007783:Lactones; D013440:Sulfides; C476502:alpha-methyl-D-serine-beta-lactone; D012694:Serine; C001520:lanthionine; D003545:Cysteine; D000409:Alanine