Organic Letters 2013-09-06

Bioreduction of aryl azides during mutasynthesis of new ansamitocins.

Lena Mancuso, Gerrit Jürjens, Jekaterina Hermane, Kirsten Harmrolfs, Simone Eichner, Jörg Fohrer, Wera Collisi, Florenz Sasse, Andreas Kirschning

Index: Org. Lett. 15(17) , 4442-5, (2013)

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Abstract

Supplementing a culture of a mutant strain of Actinosynnema pretiosum that is unable to biosynthesize aminohydroxy benzoic acid (AHBA), with 3-azido-5-hydroxy-benzoic acid and 3-azido-5-amino-benzoic acid, unexpectedly yielded anilino ansamitocins instead of the expected azido derivatives. This is the first example of the bioreduction of organic azides. The unique nature of these results was demonstrated when 3-azido-5-amino-benzoic acid was fed to the corresponding AHBA blocked mutant of Streptomyces hygroscopicus, the geldanamycin producer. This mutasynthetic experiment yielded the fully processed azido derivative of geldanamycin.