141527-78-8Relevant articles and documents
Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli
Denoel, Thibaut,Zervosen, Astrid,Gerards, Thomas,Lemaire, Christian,Joris, Bernard,Blanot, Didier,Luxen, Andre
, p. 4621 - 4628 (2014/10/16)
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 35S. 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-[35S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.
The synthesis of chiral 3-oxo-6-[(phenylmethoxy)-carbonyl]-2-piperazineacetic acid esters designed for the presentation of an aspartic acid side chain. A subsequent novel Friedel Crafts reaction
Kogan,Rawson
, p. 7089 - 7092 (2007/10/02)
The syntheses of (2S, 6R)-, and (2S, 6S)-3-oxo-6-[(phenylmethoxy)carbonyl]-2-piperazineacetic acid methyl esters from L- or D-serine and dimethyl-D-malate are described. Acylation of the (2S, 6S) isomer with 3-methoxyphenylacetyl chloride, hydrogenolysis of the benzyl ester, followed by treatment with oxalyl chloride then aluminum chloride led to an unexpected tricyclic product into which a C2O2 unit had been incorporated.
