Literature DB >> 18037983

Differentiation of chiral phosphorus enantiomers by P and H NMR spectroscopy using amino acid derivatives as chemical solvating agents.

Yingchun Li1, Frank M Raushel.   

Abstract

The ability of commercially available amino acid derivatives, especially Fmoc-Trp(Boc)-OH, to differentiate enantiomers of chiral phosphonates, phosphinates, phosphates, phosphine oxides, and phosphonamidates is demonstrated with (31)P, (13)C, and (1)H NMR spectroscopy. The chiral differentiation provided a rapid and convenient method for measuring the enantiomeric purity of these phosphorus compounds.

Entities:  

Year:  2007        PMID: 18037983      PMCID: PMC2084221          DOI: 10.1016/j.tetasy.2007.06.012

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN: 0957-4166


  12 in total

1.  Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues.

Authors:  M Chen-Goodspeed; M A Sogorb; F Wu; F M Raushel
Journal:  Biochemistry       Date:  2001-02-06       Impact factor: 3.162

Review 2.  Emerging methods for the rapid determination of enantiomeric excess.

Authors:  M G Finn
Journal:  Chirality       Date:  2002-07       Impact factor: 2.437

3.  Predicting substrates by docking high-energy intermediates to enzyme structures.

Authors:  Johannes C Hermann; Eman Ghanem; Yingchun Li; Frank M Raushel; John J Irwin; Brian K Shoichet
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

4.  Stereochemical constraints on the substrate specificity of phosphotriesterase.

Authors:  S B Hong; F M Raushel
Journal:  Biochemistry       Date:  1999-01-26       Impact factor: 3.162

5.  Resolution of chiral phosphate, phosphonate, and phosphinate esters by an enantioselective enzyme library.

Authors:  Charity Nowlan; Yingchun Li; Johannes C Hermann; Timothy Evans; Joseph Carpenter; Eman Ghanem; Brian K Shoichet; Frank M Raushel
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

6.  Stereoselective detoxification of chiral sarin and soman analogues by phosphotriesterase.

Authors:  W S Li; K T Lum; M Chen-Goodspeed; M A Sogorb; F M Raushel
Journal:  Bioorg Med Chem       Date:  2001-08       Impact factor: 3.641

Review 7.  Toxicological assessment of isomeric pesticides: a strategy for testing of chiral organophosphorus (OP) compounds for delayed polyneuropathy in a regulatory setting.

Authors:  Jon M Battershill; Philippa M Edwards; Martin K Johnson
Journal:  Food Chem Toxicol       Date:  2004-08       Impact factor: 6.023

8.  Organophosphates, serine esterase inhibition, and modeling of organophosphate toxicity.

Authors:  Janice Chambers; Seth F Oppenheimer
Journal:  Toxicol Sci       Date:  2004-02       Impact factor: 4.849

9.  Organophosphate nerve agent toxicity in Hydra attenuata.

Authors:  Karin T Lum; Henry J Huebner; Yingchun Li; Timothy D Phillips; Frank M Raushel
Journal:  Chem Res Toxicol       Date:  2003-08       Impact factor: 3.739

Review 10.  Organophosphorus ester-induced delayed neurotoxicity.

Authors:  M B Abou-Donia
Journal:  Annu Rev Pharmacol Toxicol       Date:  1981       Impact factor: 13.820

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  4 in total

1.  Stereoselective Formation of Multiple Reaction Products by the Phosphotriesterase from Sphingobium sp. TCM1.

Authors:  Andrew N Bigley; Tamari Narindoshvili; Dao Feng Xiang; Frank M Raushel
Journal:  Biochemistry       Date:  2020-03-17       Impact factor: 3.162

2.  Stereoselective hydrolysis of organophosphate nerve agents by the bacterial phosphotriesterase.

Authors:  Ping-Chuan Tsai; Andrew Bigley; Yingchun Li; Eman Ghanem; C Linn Cadieux; Shane A Kasten; Tony E Reeves; Douglas M Cerasoli; Frank M Raushel
Journal:  Biochemistry       Date:  2010-09-21       Impact factor: 3.162

3.  A 1-phytase type III effector interferes with plant hormone signaling.

Authors:  Doreen Blüher; Debabrata Laha; Sabine Thieme; Alexandre Hofer; Lennart Eschen-Lippold; Antonia Masch; Gerd Balcke; Igor Pavlovic; Oliver Nagel; Antje Schonsky; Rahel Hinkelmann; Jakob Wörner; Nargis Parvin; Ralf Greiner; Stefan Weber; Alain Tissier; Mike Schutkowski; Justin Lee; Henning Jessen; Gabriel Schaaf; Ulla Bonas
Journal:  Nat Commun       Date:  2017-12-18       Impact factor: 14.919

Review 4.  Recent Advances in Multinuclear NMR Spectroscopy for Chiral Recognition of Organic Compounds.

Authors:  Márcio S Silva
Journal:  Molecules       Date:  2017-02-07       Impact factor: 4.411

  4 in total

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