4ld7

Structural highlights

Function

ANAPT_NEOFI Indole diterpene prenyltransferase; part of the gene cluster that mediates the biosynthesis of the prenylated pyrroloindoline diketopiperazine acetylaszonalenin (PubMed:19001367). The first step in the pathway is the formation of (R)-benzodiazepinedione by condensation of tryptophan and anthranilic acid catalyzed by the non-ribosomal peptide synthetase anaPS (PubMed:19001367). The prenyltransferase anaPT then converts (R)-benzodiazepinedione to aszonalenin in the presence of dimethylallyl diphosphate (DMAPP) via C3-prenylation (PubMed:19001367, PubMed:19421461, PubMed:20165805, PubMed:24014429, PubMed:26294262). The last step in the biosynthesis of acetylaszonalenin via acetylation of aszonalenin at position N1 catalyzed by anaAT (PubMed:19001367, PubMed:20165805).^{[1] [2] [3] [4] [5]}

See Also

• Tryptophan synthase 3D structures

References

1. ↑ Yin WB, Grundmann A, Cheng J, Li SM. Acetylaszonalenin biosynthesis in Neosartorya fischeri. Identification of the biosynthetic gene cluster by genomic mining and functional proof of the genes by biochemical investigation. J Biol Chem. 2009 Jan 2;284(1):100-109. doi: 10.1074/jbc.M807606200. Epub 2008 , Nov 10. PMID:19001367 doi:http://dx.doi.org/10.1074/jbc.M807606200
2. ↑ Yin WB, Cheng J, Li SM. Stereospecific synthesis of aszonalenins by using two recombinant prenyltransferases. Org Biomol Chem. 2009 May 21;7(10):2202-7. doi: 10.1039/b902413a. Epub 2009 Apr , 3. PMID:19421461 doi:http://dx.doi.org/10.1039/b902413a
3. ↑ Yin WB, Xie XL, Matuschek M, Li SM. Reconstruction of pyrrolo[2,3-b]indoles carrying an alpha-configured reverse C3-dimethylallyl moiety by using recombinant enzymes. Org Biomol Chem. 2010 Mar 7;8(5):1133-41. doi: 10.1039/b922440h. Epub 2010 Jan 7. PMID:20165805 doi:http://dx.doi.org/10.1039/b922440h
4. ↑ Pockrandt D, Li SM. Geranylation of cyclic dipeptides by the dimethylallyl transferase AnaPT resulting in a shift of prenylation position on the indole ring. Chembiochem. 2013 Oct 11;14(15):2023-8. doi: 10.1002/cbic.201300372. Epub 2013 , Sep 6. PMID:24014429 doi:http://dx.doi.org/10.1002/cbic.201300372
5. ↑ Zhou K, Yu X, Xie X, Li SM. Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases. J Nat Prod. 2015 Sep 25;78(9):2229-35. doi: 10.1021/acs.jnatprod.5b00422. Epub , 2015 Aug 21. PMID:26294262 doi:http://dx.doi.org/10.1021/acs.jnatprod.5b00422