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Silver(I)‐Catalyzed Route to Pyrroles: Synthesis of Halogenated Pseudilins as Allosteric Inhibitors for Myosin ATPase and X‐ray Crystal Structures of the Protein–Inhibitor Complexes
Author(s) -
Martin René,
Risacher Célia,
Barthel André,
Jäger Anne,
Schmidt Arndt W.,
Richter Sabine,
Böhl Markus,
Preller Matthias,
Chinthalapudi Krishna,
Manstein Dietmar J.,
Gutzeit Herwig O.,
Knölker HansJoachim
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402177
Subject(s) - chemistry , allosteric regulation , cycloisomerization , atpase , gene isoform , myosin , catalysis , stereochemistry , enzyme , biochemistry , gene
The pentahalogenated 2‐arylpyrrole‐type alkaloids pentabromopseudilin and pentachloropseudilin represent a new class of isoform‐specific allosteric inhibitors of myosin ATPase. Herein, we describe an application of the silver(I)‐catalyzed cycloisomerization of N ‐(homopropargyl)toluenesulfonamides to the total syntheses of these natural products and several non‐natural analogues. Moreover, we examine the inhibitiory effect of pentahalogenated pseudilins on myosin ATPase activity.