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  • Title: Stereoselective synthesis of orthogonally protected alpha-methylnorlanthionine.
    Author: Avenoza A, Busto JH, Jiménez-Osés G, Peregrina JM.
    Journal: Org Lett; 2006 Jun 22; 8(13):2855-8. PubMed ID: 16774274.
    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.
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