title: Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli.
abstract: The three diastereoisomers-(R,R), (S,S) and meso-of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with (35)S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[(35)S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.
authors.affiliation: Centre de Recherches du Cyclotron, Université de Liège, Allée du 6 Août 8, Bât B30, B-4000 Sart-Tilman, Liège, Belgium.
authors.forename: Thibaut
authors.initials: T
authors.lastname: Denoël
authors.affiliation: Centre de Recherches du Cyclotron, Université de Liège, Allée du 6 Août 8, Bât B30, B-4000 Sart-Tilman, Liège, Belgium. Electronic address: azervosen@ulg.ac.be.
authors.forename: Astrid
authors.initials: A
authors.lastname: Zervosen
authors.affiliation: Centre de Recherches du Cyclotron, Université de Liège, Allée du 6 Août 8, Bât B30, B-4000 Sart-Tilman, Liège, Belgium.
authors.forename: Thomas
authors.initials: T
authors.lastname: Gerards
authors.affiliation: Centre de Recherches du Cyclotron, Université de Liège, Allée du 6 Août 8, Bât B30, B-4000 Sart-Tilman, Liège, Belgium.
authors.forename: Christian
authors.initials: C
authors.lastname: Lemaire
authors.affiliation: Centre d'Ingénierie des Protéines, Université de Liège, Institut de Chimie, Bât B6, B-4000 Sart-Tilman, Liège, Belgium.
authors.forename: Bernard
authors.initials: B
authors.lastname: Joris
authors.affiliation: Enveloppes Bactériennes et Antibiotiques, UMR 8619 CNRS, Univ Paris-Sud, Bât 430, 91405 Orsay, France.
authors.forename: Didier
authors.initials: D
authors.lastname: Blanot
authors.affiliation: Centre de Recherches du Cyclotron, Université de Liège, Allée du 6 Août 8, Bât B30, B-4000 Sart-Tilman, Liège, Belgium.
authors.forename: André
authors.initials: A
authors.lastname: Luxen
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D004926:Escherichia coli / Q000737:chemistry / Q000254:growth & development / Q000378:metabolism*; D015394:Molecular Structure; D010457:Peptidoglycan / Q000737:chemistry* / Q000378:metabolism*; D012996:Solutions; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D014867:Water / Q000737:chemistry / Q000378:metabolism
chemical_list: D010457:Peptidoglycan; D012996:Solutions; D013440:Sulfides; D014867:Water; C001520:lanthionine; D000409:Alanine
keywords: Alanine β-cation; Lanthionine; Peptidoglycan; Serine; Sulfamidate