Literature DB >> 19727329

An Enantioselective Synthesis of (S)-4-Fluorohistidine.

Jan Hajduch1, John C Cramer, Kenneth L Kirk.   

Abstract

We report a new synthesis of enantiomerically pure (S)-4-fluorohisitidine based on diastereoselective alkylation of MOM-protected 4-fluoro-5-bromomethyl imidazole using the Schöllkopf bis-lactim amino acid synthesis. Improvements in procedures for preparation of key intermediates are also described. (S)-4-Fluorohisitidine prepared by this new method was identical in all respects to material prepared by previous procedures.

Entities:  

Year:  2008        PMID： 19727329      PMCID： PMC2598420          DOI： 10.1016/j.jfluchem.2008.04.011

Source DB:  PubMed          Journal:  J Fluor Chem        ISSN： 0022-1139            Impact factor:   2.050


  9 in total

1.  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

2.  Active site ligand binding by an inactive ribonuclease S analogue. A quantitative affinity chromatographic study.

Authors:  H C Taylor; I M Chaiken
Journal:  J Biol Chem       Date:  1977-10-25       Impact factor: 5.157

3.  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

4.  Photochemistry of diazonium salts. 3. A new and facile synthesis of 4-fluoroimidazoles.

Authors:  K L Kirk; L A Cohen
Journal:  J Org Chem       Date:  1973-10-05       Impact factor: 4.354

5.  Photochemical decomposition of diazonium fluoroborates. Application to the synthesis of ring-fluorinated imidazoles.

Authors:  K L Kirk; L A Cohen
Journal:  J Am Chem Soc       Date:  1971-06-16       Impact factor: 15.419

6.  Photochemistry of diazonium salts. II. Synthesis of 2-fluoro-L-histidine and 2-fluorohistamine, and the halogen lability of 2-fluoroimidazoles.

Authors:  K L Kirk; W Nagai; L A Cohen
Journal:  J Am Chem Soc       Date:  1973-12-12       Impact factor: 15.419

7.  Photochemical Schiemann Reaction in Ionic Liquids.

Authors:  Jorge Heredia-Moya; Kenneth L Kirk
Journal:  J Fluor Chem       Date:  2007-06       Impact factor: 2.050

8.  Nuclear magnetic resonance and molecular genetic studies of the membrane-bound D-lactate dehydrogenase of Escherichia coli.

Authors:  G S Rule; E A Pratt; V Simplaceanu; C Ho
Journal:  Biochemistry       Date:  1987-01-27       Impact factor: 3.162

9.  A designed peptide ligase for total synthesis of ribonuclease A with unnatural catalytic residues.

Authors:  D Y Jackson; J Burnier; C Quan; M Stanley; J Tom; J A Wells
Journal:  Science       Date:  1994-10-14       Impact factor: 47.728
  9 in total
  1 in total

1.  The Biophysical Probes 2-fluorohistidine and 4-fluorohistidine: Spectroscopic Signatures and Molecular Properties.

Authors:  Chandana Kasireddy; Jonathan M Ellis; James G Bann; Katie R Mitchell-Koch
Journal:  Sci Rep       Date:  2017-02-15       Impact factor: 4.379
  1 in total

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