title: S-Michael additions to chiral dehydroalanines as an entry to glycosylated cysteines and a sulfa-Tn antigen mimic.
abstract: Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(β-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.
authors.affiliation: Departamento de Química, Universidad de La Rioja , Centro de Investigación en Síntesis Química, E-26006 Logroño, Spain.
authors.forename: Carlos
authors.initials: C
authors.lastname: Aydillo
authors.forename: Ismael
authors.initials: I
authors.lastname: Compañón
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.forename: Francisco
authors.initials: F
authors.lastname: Corzana
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
authors.forename: María M
authors.initials: MM
authors.lastname: Zurbano
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D003545:Cysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D003958:Diamide / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D015295:Antigens, Tumor-Associated, Carbohydrate; D002241:Carbohydrates; C040286:Tn antigen; D003958:Diamide; C015102:dehydroalanine; D003545:Cysteine; D000409:Alanine