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==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== | |||
<StructureSection load='3v1s' size='340' side='right' caption='[[3v1s]], [[Resolution|resolution]] 2.33Å' scene=''> | |||
== Structural highlights == | |||
<table><tr><td colspan='2'>[[3v1s]] is a 2 chain structure with sequence from [http://en.wikipedia.org/wiki/Rauvolfia_serpentina Rauvolfia serpentina]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=3V1S OCA]. For a <b>guided tour on the structure components</b> use [http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=3V1S FirstGlance]. <br> | |||
</td></tr><tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat"><scene name='pdbligand=0LH:2-(1H-INDOL-1-YL)ETHANAMINE'>0LH</scene></td></tr> | |||
<tr id='gene'><td class="sblockLbl"><b>[[Gene|Gene:]]</b></td><td class="sblockDat">STR1 ([http://www.ncbi.nlm.nih.gov/Taxonomy/Browser/wwwtax.cgi?mode=Info&srchmode=5&id=4060 Rauvolfia serpentina])</td></tr> | |||
<tr id='activity'><td class="sblockLbl"><b>Activity:</b></td><td class="sblockDat"><span class='plainlinks'>[http://en.wikipedia.org/wiki/Strictosidine_synthase Strictosidine synthase], with EC number [http://www.brenda-enzymes.info/php/result_flat.php4?ecno=4.3.3.2 4.3.3.2] </span></td></tr> | |||
<tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[http://oca.weizmann.ac.il/oca-docs/fgij/fg.htm?mol=3v1s FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=3v1s OCA], [http://www.rcsb.org/pdb/explore.do?structureId=3v1s RCSB], [http://www.ebi.ac.uk/pdbsum/3v1s PDBsum]</span></td></tr> | |||
</table> | |||
<div style="background-color:#fffaf0;"> | |||
== Publication Abstract from PubMed == | |||
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. | |||
Scaffold Tailoring by a Newly Detected Pictet-Spenglerase Activity of Strictosidine Synthase: From the Common Tryptoline Skeleton to the Rare Piperazino-indole Framework.,Wu F, Zhu H, Sun L, Rajendran C, Wang M, Ren X, Panjikar S, Cherkasov A, Zou H, Stockigt J J Am Chem Soc. 2012 Jan 25;134(3):1498-500. Epub 2012 Jan 9. PMID:22229634<ref>PMID:22229634</ref> | |||
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.<br> | |||
</div> | |||
==See Also== | ==See Also== | ||
*[[Strictosidine Synthase|Strictosidine Synthase]] | *[[Strictosidine Synthase|Strictosidine Synthase]] | ||
== References == | |||
== | <references/> | ||
< | __TOC__ | ||
</StructureSection> | |||
[[Category: Rauvolfia serpentina]] | [[Category: Rauvolfia serpentina]] | ||
[[Category: Strictosidine synthase]] | [[Category: Strictosidine synthase]] | ||
[[Category: Cherkasov, A | [[Category: Cherkasov, A]] | ||
[[Category: Panjikar, S | [[Category: Panjikar, S]] | ||
[[Category: Rajendran, C | [[Category: Rajendran, C]] | ||
[[Category: Ren, X | [[Category: Ren, X]] | ||
[[Category: Stoeckigt, J | [[Category: Stoeckigt, J]] | ||
[[Category: Sun, L | [[Category: Sun, L]] | ||
[[Category: Wang, M | [[Category: Wang, M]] | ||
[[Category: Wu, F | [[Category: Wu, F]] | ||
[[Category: Zhu, H | [[Category: Zhu, H]] | ||
[[Category: Zou, H | [[Category: Zou, H]] | ||
[[Category: Alkaloid biosynthesis]] | [[Category: Alkaloid biosynthesis]] | ||
[[Category: Lyase]] | [[Category: Lyase]] | ||
[[Category: Strictosidine synthase family]] | [[Category: Strictosidine synthase family]] | ||
Revision as of 11:42, 18 December 2014
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 frameworkScaffold 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
Structural highlights
Publication Abstract from PubMedThe 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. Scaffold Tailoring by a Newly Detected Pictet-Spenglerase Activity of Strictosidine Synthase: From the Common Tryptoline Skeleton to the Rare Piperazino-indole Framework.,Wu F, Zhu H, Sun L, Rajendran C, Wang M, Ren X, Panjikar S, Cherkasov A, Zou H, Stockigt J J Am Chem Soc. 2012 Jan 25;134(3):1498-500. Epub 2012 Jan 9. PMID:22229634[1] From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine. See AlsoReferences
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