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Genetic incorporation of 4-fluorohistidine into peptides enables selective affinity purification.


ABSTRACT: Due to the lowered pKa of 4-fluorohistidine relative to histidine, peptides and proteins containing this amino acid are potentially endowed with novel properties. We report here the optimized synthesis of 4-fluorohistidine and show that it can efficiently replace histidine in in vitro translation reactions. Moreover, peptides containing 6×-fluorohistidine tags are able to be selectively captured and eluted from nickel resin in the presence of his-tagged protein mixtures.

SUBMITTER: Ring CM 

PROVIDER: S-EPMC6010304 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Genetic incorporation of 4-fluorohistidine into peptides enables selective affinity purification.

Ring Christine M CM   Iqbal Emil S ES   Hacker David E DE   Hartman Matthew C T MCT   Cropp T Ashton TA  

Organic & biomolecular chemistry 20170501 21


Due to the lowered pK<sub>a</sub> of 4-fluorohistidine relative to histidine, peptides and proteins containing this amino acid are potentially endowed with novel properties. We report here the optimized synthesis of 4-fluorohistidine and show that it can efficiently replace histidine in in vitro translation reactions. Moreover, peptides containing 6×-fluorohistidine tags are able to be selectively captured and eluted from nickel resin in the presence of his-tagged protein mixtures. ...[more]

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