4RNQ

Crystal structure of tobacco 5-epi-aristolochene synthase (TEAS) with anilinogeranyl diphosphate (AGPP) and geraniline

4RNQ の概要

• エントリーDOI: 10.2210/pdb4rnq/pdb
• 分子名称: 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)
• 機能のキーワード: teas, 5-epi-aristolochene synthase, anilinogeranyl diphosphate (agpp), geraniline, terpene synthase, lyase
• 由来する生物種: Nicotiana tabacum (American tobacco,tobacco)
• 細胞内の位置: Cytoplasm: Q40577
• タンパク質・核酸の鎖数: 1
• 化学式量合計: 64140.27

構造登録者

Koo, H.J.,Crenshaw, C.M.,Starks, C.,Spielmann, H.P.,Chappell, J.,Noel, J.P. (登録日: 2014-10-24, 公開日: 2015-05-06, 最終更新日: 2024-02-28)

主引用文献

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

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: 25897591
DOI: 10.1021/acschembio.5b00145

実験手法

X-RAY DIFFRACTION (2.47 Å)