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Asymmetric synthesis of first generation molecular motors.

ABSTRACT: A general enantioselective route to functionalized first generation molecular motors is described. An enantioselective protonation of the silyl enol ethers of indanones by a Au(I)BINAP complex sets the stage for a highly diastereoselective McMurry coupling as a second enhancement step for enantiomeric excess. In this way various functionalized overcrowded alkenes could be synthesized in good yields (up to 78%) and good to excellent enantiomeric excess (85% ee->98% ee) values.

SUBMITTER: Neubauer TM

PROVIDER: S-EPMC5055213 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of first generation molecular motors.

Neubauer Thomas M TM van Leeuwen Thomas T Zhao Depeng D Lubbe Anouk S AS Kistemaker Jos C M JC Feringa Ben L BL

Organic letters 20140731 16

A general enantioselective route to functionalized first generation molecular motors is described. An enantioselective protonation of the silyl enol ethers of indanones by a Au(I)BINAP complex sets the stage for a highly diastereoselective McMurry coupling as a second enhancement step for enantiomeric excess. In this way various functionalized overcrowded alkenes could be synthesized in good yields (up to 78%) and good to excellent enantiomeric excess (85% ee->98% ee) values. ...[more]

PMID: 25079823

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Project description:Many active cellular processes such as long-distance cargo transport, spindle organization, as well as flagellar and ciliary beating are driven by molecular motors. These motor proteins act collectively and typically work in small teams. One particularly interesting example is two teams of antagonistic motors that pull a common cargo into opposite directions, thereby generating mutual interaction forces. Important issues regarding such multiple motor systems are whether or not motors from the same team share their load equally, and how the collectively generated forces depend on the single motor properties. Here we address these questions by introducing a stochastic model for cargo transport by an arbitrary number of elastically coupled molecular motors. We determine the state space of this motor system and show that this space has a rather complex and nested structure, consisting of multiple activity states and a large number of elastic substates, even for the relatively small system of two identical motors working against one antagonistic motor. We focus on this latter case because it represents the simplest tug-of-war that involves force sharing between motors from the same team. We show that the most likely motor configuration is characterized by equal force sharing between identical motors and that the most likely separation of these motors corresponds to a single motor step. These likelihoods apply to different types of motors and to different elastic force potentials acting between the motors. Furthermore, these features are observed both in the steady state and during the initial build-up of elastic strains. The latter build-up is non-monotonic and exhibits a maximum at intermediate times, a striking consequence of mutual unbinding of the elastically coupled motors. Mutual strain-induced unbinding also reduces the magnitude of the collectively generated forces. Our computational approach is quite general and can be extended to other motor systems such as motor teams working against an optical trap or mixed teams of motors with different single motor properties.

Dataset Information

Asymmetric synthesis of first generation molecular motors.

Publications

Asymmetric synthesis of first generation molecular motors.

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