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Cyclization of Synthetic seco ‐Proansamitocins to Ansamitocin Macrolactams by Actinosynnema pretiosum as Biocatalyst
Author(s) -
Harmrolfs Kirsten,
Brünjes Marco,
Dräger Gerald,
Floss Heinz G.,
Sasse Florenz,
Taft Florian,
Kirschning Andreas
Publication year - 2010
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201000422
Subject(s) - stereochemistry , amide , chemistry , biocatalysis , diterpene , computational biology , biochemistry , biology , catalysis , ionic liquid
Ring closure is possible with seco ‐proansamitocin and two activated SNAC esters, which can be processed to ansamitocin P3 and 19‐deschloro‐20‐demethoxy AP‐3, respectively, by an AHBA‐blocked mutant of Actinosynnema pretiosum. This work sheds light on the synthetic potential of macrolactamizing amide synthases. The new ansamitocin derivative showed similar to enhanced antiproliferative activity against several cancer cell lines relative to AP‐3.