Stereoselective synthesis of orthogonally protected alpha-methylnorlanthionine.
[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.
Avenoza
Alberto
A
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, UA-CSIC, Logroño, Spain. alberto.avenoza@dq.unirioja.es
Busto
Jesús H
JH
Jiménez-Osés
Gonzalo
G
Peregrina
Jesús M
JM
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
D000596:Amino Acids; D010456:Peptides, Cyclic; D013440:Sulfides; D009561:Nisin; C001520:lanthionine; D003545:Cysteine; D000409:Alanine