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The Interplay between Mutasynthesis and Semisynthesis: Generation and Evaluation of an Ansamitocin Library
Author(s) -
Eichner Simone,
Knobloch Tobias,
Floss Heinz G.,
Fohrer Jörg,
Harmrolfs Kirsten,
Hermane Jekaterina,
Schulz Anne,
Sasse Florenz,
Spiteller Peter,
Taft Florian,
Kirschning Andreas
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106249
Subject(s) - semisynthesis , moiety , geldanamycin , polyketide , chemistry , stereochemistry , computational biology , biosynthesis , biology , biochemistry , gene , heat shock protein , hsp90
Working hand in hand! The synthetic power of three mutant strains that produce ansamitocin and geldanamycin is combined with chemical synthesis, thus leading to 27 new ansamitocin derivatives. Structure–activity studies show that the N of the carbinolamide moiety is not important for cytotoxic activity but the α orientation of the OH group at C9 is key [see structures; chemical synthesis (red), mutasynthesis (blue), biosynthesis (black)].