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De novo synthesis of alkyne substituted tryptophans as chemical probes for protein profiling studies.

ABSTRACT: De novo synthesis of alkynalted tryptophan moieties as chemical probes for protein profilling studies, via an unexpected synthesis of Michael acceptor 12 is reported. Friedel Craft's alkylation of 12 and alkyne substituted indoles gave alkynalated tryptophan moieties, which perform as chemical probe by incorporating into actively translating Escherichia coli cells, whereby the alkyne moiety enables multimodal analyses through click chemistry mediated attachment of reporting groups.

SUBMITTER: Nair RN 

PROVIDER: S-EPMC5607013 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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<i>De novo</i> synthesis of alkyne substituted tryptophans as chemical probes for protein profiling studies.

Nair R N RN   Rosnow J J JJ   Murphree T A TA   Bowden M E ME   Lindemann S R SR   Wright A T AT  

Organic chemistry frontiers : an international journal of organic chemistry 20161226 4

<i>De novo</i> synthesis of alkynalted tryptophan moieties as chemical probes for protein profilling studies, via an unexpected synthesis of Michael acceptor 12 is reported. Friedel Craft's alkylation of 12 and alkyne substituted indoles gave alkynalated tryptophan moieties, which perform as chemical probe by incorporating into actively translating <i>Escherichia coli</i> cells, whereby the alkyne moiety enables multimodal analyses through click chemistry mediated attachment of reporting groups. ...[more]

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