title: Stereoselective synthesis of orthogonally protected alpha-methylnorlanthionine.
abstract: [reaction: see text] As the unusual amino acid norlanthionine (nor-Lan) has previously been incorporated into cyclic peptide analogues of the ring C of lantibiotic nisin, we report here the stereoselective synthesis of the new (S,R)- and (R,R)-alpha-methylnorlanthionines (alpha-Me-nor-Lan). The orthogonally protected derivatives of these compounds have also been prepared. The key step in the synthesis of these bisamino acids was the S(N)2 opening reaction of the corresponding cyclic sulfamidates with the SH group of appropriately protected l-cysteine derivatives.
authors.affiliation: Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, UA-CSIC, Logroño, Spain. alberto.avenoza@dq.unirioja.es
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Jiménez-Osés
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003545:Cysteine / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009561:Nisin / Q000737:chemistry; D010456:Peptides, Cyclic / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D010456:Peptides, Cyclic; D013440:Sulfides; D009561:Nisin; C001520:lanthionine; D003545:Cysteine; D000409:Alanine