3V1S

Scaffold tailoring by a newly detected Pictet-Spenglerase ac-tivity of strictosidine synthase (STR1): from the common tryp-toline skeleton to the rare piperazino-indole framework

3V1S の概要

• エントリーDOI: 10.2210/pdb3v1s/pdb
• 分子名称: Strictosidine synthase, 2-(1H-indol-1-yl)ethanamine (3 entities in total)
• 機能のキーワード: strictosidine synthase, alkaloid biosynthesis, strictosidine synthase family, lyase
• 由来する生物種: Rauvolfia serpentina (devilpepper)
• 細胞内の位置: Vacuole: P68175
• タンパク質・核酸の鎖数: 2
• 化学式量合計: 71852.31

構造登録者

Wu, F.,Zhu, H.,Sun, L.,Rajendran, C.,Wang, M.,Ren, X.,Panjikar, S.,Cherkasov, A.,Zou, H.,Stoeckigt, J. (登録日: 2011-12-10, 公開日: 2012-02-29, 最終更新日: 2024-10-30)

主引用文献

Wu, F.,Zhu, H.,Sun, L.,Rajendran, C.,Wang, M.,Ren, X.,Panjikar, S.,Cherkasov, A.,Zou, H.,Stockigt, J.
Scaffold Tailoring by a Newly Detected Pictet-Spenglerase Activity of Strictosidine Synthase: From the Common Tryptoline Skeleton to the Rare Piperazino-indole Framework
J.Am.Chem.Soc., 134:1498-1500, 2012

PubMed Abstract: The Pictet-Spenglerase strictosidine synthase (STR1) has been recognized as a key enzyme in the biosynthesis of some 2000 indole alkaloids in plants, some with high therapeutic value. In this study, a novel function of STR1 has been detected which allows for the first time a simple enzymatic synthesis of the strictosidine analogue 3 harboring the piperazino[1,2-a]indole (PI) scaffold and to switch from the common tryptoline (hydrogenated carboline) to the rare PI skeleton. Insight into the reaction is provided by X-ray crystal analysis and modeling of STR1 ligand complexes. STR1 presently provides exclusively access to 3 and can act as a source to generate by chemoenzymatic approaches libraries of this novel class of alkaloids which may have new biological activities. Synthetic or natural monoterpenoid alkaloids with the PI core have not been reported before.

PubMed: 22229634
DOI: 10.1021/ja211524d

実験手法

X-RAY DIFFRACTION (2.328 Å)