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Myxochelins B, C, D, E and F: A New Structural Principle for Powerful Siderophores Imitating Nature
Author(s) -
Ambrosi HorstDieter,
Hartmann Vera,
Pistorius Daniel,
Reissbrodt Rolf,
TrowitzschKienast Wolfram
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199803)1998:3<541::aid-ejoc541>3.0.co;2-a
Subject(s) - siderophore , chemistry , amide , stereochemistry , enantiomer , combinatorial chemistry , organic chemistry , biochemistry , gene
The synthesis of the natural siderophore myxochelin B ( 1 S ) and its enantiomer 1 R is described. 1 S and 1 R served as precursors for the synthesis of new hexa dentate siderophores, the myxochelins C ( 7 S ) and C R ( 7 R ), D ( 14 S ) and D R ( 14 R ), E ( 19 S ) and ( RS )‐F ( 26 R, S ), with 2,3‐dihydroxybenzoate (DHB) ligands and the simple backbones of asymmetric 1,2, n ‐triamino‐ n ‐alkanes. For the myxochelins C, D, E and F n is 6 (from lysine), 5 (from ornithin), 4 (from asparagine amide) and 7 [from (±)‐2‐aminopimelic acid], respectively. The additional amino functions in the starting compounds were provided by dehydration of the corresponding primary amides, and subsequent reduction of the nitriles by cobalt boride in methanol. All new siderophores supply bacteria with ferric ions with an efficiency which depends on their chain length and stereochemistry. They show significant activity against the cytomegalo virus.