Details
| Original language | English |
|---|---|
| Pages (from-to) | 4442-4445 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 15 |
| Issue number | 17 |
| Publication status | Published - 27 Aug 2013 |
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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 15, No. 17, 27.08.2013, p. 4442-4445.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Bioreduction of aryl azides during mutasynthesis of new ansamitocins
AU - Mancuso, Lena
AU - Jürjens, Gerrit
AU - Hermane, Jekaterina
AU - Harmrolfs, Kirsten
AU - Eichner, Simone
AU - Fohrer, Jörg
AU - Collisi, Wera
AU - Sasse, Florenz
AU - Kirschning, Andreas
PY - 2013/8/27
Y1 - 2013/8/27
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84883748130&partnerID=8YFLogxK
U2 - 10.1021/ol401989e
DO - 10.1021/ol401989e
M3 - Article
C2 - 23981134
AN - SCOPUS:84883748130
VL - 15
SP - 4442
EP - 4445
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 17
ER -