Literature DB >> 28517015

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

Christine M Ring1, Emil S Iqbal, David E Hacker, Matthew C T Hartman, T Ashton Cropp.   

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.

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Year:  2017        PMID： 28517015      PMCID： PMC6010304          DOI： 10.1039/c7ob00844a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  20 in total

1.  Cell-free translation reconstituted with purified components.

Authors:  Y Shimizu; A Inoue; Y Tomari; T Suzuki; T Yokogawa; K Nishikawa; T Ueda
Journal:  Nat Biotechnol       Date:  2001-08       Impact factor: 54.908

2.  Programming peptidomimetic syntheses by translating genetic codes designed de novo.

Authors:  Anthony C Forster; Zhongping Tan; Madhavi N L Nalam; Hening Lin; Hui Qu; Virginia W Cornish; Stephen C Blacklow
Journal:  Proc Natl Acad Sci U S A       Date:  2003-05-16       Impact factor: 11.205

3.  Amino acid backbone specificity of the Escherichia coli translation machinery.

Authors:  Zhongping Tan; Anthony C Forster; Stephen C Blacklow; Virginia W Cornish
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

Review 4.  In Vitro Selection Combined with Ribosomal Translation Containing Non-proteinogenic Amino Acids.

Authors:  Tomoshige Fujino; Hiroshi Murakami
Journal:  Chem Rec       Date:  2016-01-18       Impact factor: 6.771

5.  Biosynthetic incorporation of fluorohistidine into proteins in E. coli: a new probe of macromolecular structure.

Authors:  Jack F Eichler; John C Cramer; Kenneth L Kirk; James G Bann
Journal:  Chembiochem       Date:  2005-12       Impact factor: 3.164

6.  Synthesis of polyester by means of genetic code reprogramming.

Authors:  Atsushi Ohta; Hiroshi Murakami; Eri Higashimura; Hiroaki Suga
Journal:  Chem Biol       Date:  2007-12

7.  Specificity of translation for N-alkyl amino acids.

Authors:  Baolin Zhang; Zhongping Tan; Lucas Gartenmann Dickson; Madhavi N L Nalam; Virginia W Cornish; Anthony C Forster
Journal:  J Am Chem Soc       Date:  2007-08-25       Impact factor: 15.419

8.  Photochemistry of diazonium salts. I. Synthesis of 4-fluoroimidazoles, 4-fluorohistamine, and 4-fluorohistidine.

Authors:  K L Kirk; L A Cohen
Journal:  J Am Chem Soc       Date:  1973-07-11       Impact factor: 15.419

9.  Enzymatic aminoacylation of tRNA with unnatural amino acids.

Authors:  Matthew C T Hartman; Kristopher Josephson; Jack W Szostak
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-13       Impact factor: 11.205

10.  Replacing amino acids in translation: expanding chemical diversity with non-natural variants.

Authors:  E Railey White; Timothy M Reed; Zhong Ma; Matthew C T Hartman
Journal:  Methods       Date:  2012-03-28       Impact factor: 3.608
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  1 in total

1.  Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase.

Authors:  Emil S Iqbal; Kara K Dods; Matthew C T Hartman
Journal:  Org Biomol Chem       Date:  2018-02-14       Impact factor: 3.876
  1 in total

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