4RNQ
Crystal structure of tobacco 5-epi-aristolochene synthase (TEAS) with anilinogeranyl diphosphate (AGPP) and geraniline
Summary for 4RNQ
| Entry DOI | 10.2210/pdb4rnq/pdb |
| Descriptor | 5-epi-aristolochene synthase, MAGNESIUM ION, (2E,6E)-3,7-dimethyl-8-(phenylamino)octa-2,6-dien-1-yl trihydrogen diphosphate, ... (7 entities in total) |
| Functional Keywords | teas, 5-epi-aristolochene synthase, anilinogeranyl diphosphate (agpp), geraniline, terpene synthase, lyase |
| Biological source | Nicotiana tabacum (American tobacco,tobacco) |
| Cellular location | Cytoplasm: Q40577 |
| Total number of polymer chains | 1 |
| Total formula weight | 64140.27 |
| Authors | Koo, H.J.,Crenshaw, C.M.,Starks, C.,Spielmann, H.P.,Chappell, J.,Noel, J.P. (deposition date: 2014-10-24, release date: 2015-05-06, Last modification date: 2024-02-28) |
| Primary citation | Rising, K.A.,Crenshaw, C.M.,Koo, H.J.,Subramanian, T.,Chehade, K.A.,Starks, C.,Allen, K.D.,Andres, D.A.,Spielmann, H.P.,Noel, J.P.,Chappell, J. Formation of a Novel Macrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue Anilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase. Acs Chem.Biol., 10:1729-1736, 2015 Cited by PubMed Abstract: As part of an effort to identify substrate analogs suitable for helping to resolve structural features important for terpene synthases, the inhibition of 5-epi-aristolochene biosynthesis from farnesyl diphosphate (FPP) by the tobacco 5-epi-aristolochene synthase incubated with anilinogeranyl diphosphate (AGPP) was examined. The apparent noncompetitive nature of the inhibition supported further assessment of how AGPP might be bound to crystallographic forms of the enzyme. Surprisingly, the bound form of the inhibitor appeared to have undergone a cyclization event consistent with the native mechanism associated with FPP catalysis. Biocatalytic formation of a novel 13-membered macrocyclic paracyclophane alkaloid was confirmed by high-resolution GC-MS and NMR analysis. This work provides insights into new biosynthetic means for generating novel, functionally diversified, medium-sized terpene alkaloids. PubMed: 25897591DOI: 10.1021/acschembio.5b00145 PDB entries with the same primary citation |
| Experimental method | X-RAY DIFFRACTION (2.47 Å) |
Structure validation
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