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

Summary for 3V1S

• Entry DOI: 10.2210/pdb3v1s/pdb
• Descriptor: Strictosidine synthase, 2-(1H-indol-1-yl)ethanamine (3 entities in total)
• Functional Keywords: strictosidine synthase, alkaloid biosynthesis, strictosidine synthase family, lyase
• Biological source: Rauvolfia serpentina (devilpepper)
• Cellular location: Vacuole: P68175
• Total number of polymer chains: 2
• Total formula weight: 71852.31

Authors

Wu, F.,Zhu, H.,Sun, L.,Rajendran, C.,Wang, M.,Ren, X.,Panjikar, S.,Cherkasov, A.,Zou, H.,Stoeckigt, J. (deposition date: 2011-12-10, release date: 2012-02-29, Last modification date: 2024-10-30)

Primary citation

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

Experimental method

X-RAY DIFFRACTION (2.328 Å)