Stereo and chemoselective enzymatic reduction of azido functionality: Synthesis of 4-β-aminopodophyllotoxin congeners by baker's yeast

Kamal, Ähmed; Laxminarayana, B.; Gayatri, N. Lakshmi

doi:10.1016/s0040-4039(97)01582-7

Cited by 27 publications

(2 citation statements)

References 23 publications

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“…This reduction is a rare phenomenon in nature; nitrogenases which are usually responsible for nitrogen fixation in selected classes of bacteria and archaea are able to reduce inorganic azide anions yielding N 2 and ammonia . Furthermore, there is evidence that aryl azides are prone to metabolic degradation and that Baker’s yeast is able to reduce aryl azides . Current research in our laboratories is focused on the search for this unknown biocatalyst that we expect to be present in A. pretiosum .…”

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confidence: 99%

Bioreduction of Aryl Azides during Mutasynthesis of New Ansamitocins

et al. 2013

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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.

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Bioreduction of Aryl Azides during Mutasynthesis of New Ansamitocins

et al. 2013

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“…We have also reported the synthesis of this compound by employing the methanesulfonic acid/NaI reagent system 11 and by reduction of the azido functionality by employing baker's yeast. 12 In continuation of these efforts, we herein report the synthesis of 4b-arylaminopodophyllotoxin derivatives including NPF and GL-331 by employing the BF 3 ·OEt 2 /NaI reagent system. This reagent system has recently been utilized for the iodination of alcohols but the present procedure describes the preparation of aminoaryl derivatives via the iodo intermediates.…”

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confidence: 99%