Document Detail

Concise preparation of tetra-orthogonally protected (2S,6R)-lanthionines.
MedLine Citation:
PMID:  19046137     Owner:  NLM     Status:  MEDLINE    
Lantibiotics are antimicrobial peptides containing the unique bis-amino acids lanthionine and beta-methyllanthionine. While previous syntheses of lanthionine have often involved the coupling of precursors derived from D-serine and L-cysteine, we here report an inverted strategy whereby D-cysteine and L-serine are employed as building blocks. This approach provides for a concise preparation of tetra-orthogonally protected (2R,6S)-lanthionines while allowing convenient introduction of orthogonal protecting groups not previously incorporated into lanthionines.
Nathaniel I Martin
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Jan 
Date Detail:
Created Date:  2009-01-09     Completed Date:  2009-02-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  946-9     Citation Subset:  IM    
Department of Medicinal Chemistry and Chemical Biology, University of Utrecht, Sorbonnelaan 16, 3584 CA Utrecht, The Netherlands.
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MeSH Terms
Alanine / analogs & derivatives*,  chemical synthesis,  chemistry
Bacteriocins / chemistry
Sulfides / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Bacteriocins; 0/Sulfides; 3183-08-2/lanthionine; 56-41-7/Alanine

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