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Enzymatic Racemic Resolution of a Fluorinated Substrate and Syntheses of E and Z Alkenes as Precursors for Some Biologically Active Fluorohexoses

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Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 52 Issue 3

Abstract

A fluorinated substrate 6 was prepared and then the enantiomers (6a and 7a) were separated by an enzyme in presence of an acetylating agent. The optical purity of 6a and 7a were determined by derivatising them into their MTPA -esters and then by taking their 19F NMR spectra. It was observed that, PL 266 (enzyme), benzene (solvent), 24 h (time), 40 °C (temp.) and vinyl acetate (acetylating agent) were the ideal conditions for racemic resolution. The optical purity was further improved by changing the solvent (hexane), amount of enzyme (PL 266; 3000 units), reaction time (12 h) and amount of acetylating agent (vinyl acetate; two molar). The optically pure species was used for the preparation of E and Z alkenes.

: Fluorinated Substrate; Enzymatic Racemic Resolution; Alkenes
Received: 1996-12-9
Published Online: 2014-6-2
Published in Print: 1997-3-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Calorimetrie an Yttriumtrihalogeniden und Yttriumoxidhalogemden / Calorimetry of Yttrium Trihalides and Yttrium Oxyhalides
  2. Calorimetrie an Ammoniumyttriumhalogeniden / Calorimetry of Ammonium Yttrium Halides
  3. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalysen von Tetrahalogenooxalatoosmaten (IV), [OsX4(ox)]2-, X = Cl, Br, I / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of Tetrahalogenooxalatoosmates (IV), [OsX4(ox)]2-, X = Cl, Br, I
  4. The Phenomenon of Intramolecular Attractive S---O Interactions: Synthesis and Structure of (1,10-Phenanthroline)copper(II) Complexes with Isonitroso-(4-methylthiazol-2-yl)acetamide and Isonitroso-(4-methylthiazol-2-yl)-(benzothiazol-2-yl)methanide
  5. Direct Synthesis of Zinc and Nickel(II) Complexes with 1,4-Diazabicyclo[2.2.2]octane
  6. Crystal Structure of the Di-bromo-bis(2-dimethylaminoethanolato)(dimethylsulfoxide)-copper(II)-lead(II) Dimer Obtained by Direct Synthesis
  7. Unsymmetrische BN23--Ionen in den Strukturen von Ca2ClBN2 und Sr2ClBN2 / Unsymmetric BN23--Ions in the Structures of Ca2ClBN2 and Sr2ClBN2
  8. Bromierung von „Poly(1,4-diselenobenzol)“ / Bromination of “Poly(1,4-diselenobenzene)”
  9. Monoheteroarylborate [1] / Monoheteroarylborates [1]
  10. 1,3-Di-terf-butyl-6H-benzo[b]naphtho[1,2-d]pyran-6-thione, a Severely Helically Distorted Thionolactone-Bridged Biaryl
  11. Synthese und Struktur von Kalium-4,4-difluor-[1,3,2]dithiazetidinid-1,l,3,3-tetraoxid und Rubidium-4,4,5,5-tetrafluor-[1,3,2]dithiazolidinid-1,1,3,3-tetraoxid / Syntheses and Structure of Potassium-4,4-difluoro-[1,3,2]dithiazetidinide-1,1,3,3- tetraoxide and Rubidium-4,4,5,5-tetrafluoro-[ 1,3,2]dithiazolidinide-1,1,3,3-tetraoxide
  12. Synthese und Kristallstruktur eines Barium-Zink-Vanadyl-phosphats BaZn(VO)(PO4)2 mit [(VO)PO4]-Schichten / Synthesis and Crystal Structure of a Barium-Zinc-Vanadyl-Phosphate BaZn(VO)(PO4)2 Containing [(VO)PO4] Layers
  13. Einkernige und oxoverbrückte zweikernige Fe(III)-Komplexe von N-Alkyl-N,N-bis(2-pyridylmethyl)aminen / Mononuclear and Oxo-Bridged Binuclear Fe(III) Complexes of N-Alkyl-N,N-bis(2-pyridylmethyl)amines
  14. Diphenyl(1-pyridyl)phosphine Sulfide as a Ligand in Mono-and Binuclear Coinage Metal Complexes
  15. Röntgenstrukturuntersuchungen an Elpasolith-verwandten Hexacyanokomplexen [N(CH3)4]2A[M(CN)6] (A = Rb, Tl; M = Cr, Fe) / X-Ray Structure Investigations of Elpasolite Related Hexacyano Complexes [N(CH3)4]2A[M(CN)6] (A = Rb, Tl; M = Cr, Fe)
  16. Synthese und Kristallstruktur von Hexa(tert-butyl)bismocenium-tetrachloroaluminat / Synthesis and Crystal Structure of Hexa(tert-butyl)bismocenium Tetrachloroaluminate
  17. Über die Reaktionen von (CH3)4N+I-, (CH3)4N+ICl2-, (CH3)4N+ICl4- und (CH3)4N+Cl- mit Trifluormethylhypochlorit CF3OCl / The Reactions of (CH3)4N+I-, ( CH3)4N+ICl2-, (CH3)4N+ICl4- and (CH3)4N+Cl- with Trifluoromethylhypochlorite CF3OCl
  18. Hydrothermal Synthesis and Crystal Structure of the New Manganese(II) Thioantimonate(III), Mn(en)3Sb4S7
  19. Bondenolide, a New Diterpenoid from the Seeds of Caesalpinia bonduc
  20. Enzymatic Racemic Resolution of a Fluorinated Substrate and Syntheses of E and Z Alkenes as Precursors for Some Biologically Active Fluorohexoses
  21. Synthesis and Chiroptical Properties of Some N-(2-Chloro-7-cyclopropyl-4,7-dihydro-4-oxo-thieno[2,3-b]pyridine-5-carbonyl) L-α-Amino Esters
  22. Notizen: Synthesis of N,C,C-Trilithio-2,5-diallyl-pyrrole and its Solvent-Controlled Reactions with Electrophiles Notizen
  23. Notizen: A New Lithium Amide with Bulky Substituents -Molecular Structure of N-Lithio-N-trimethylsilyl-9-amino- 9-borabicyclo[3.3.1]nonane; Competition between N-Li and BN(pp)π Interactions
https://doi.org/10.1515/znb-1997-0320

Articles in the same Issue

  1. Calorimetrie an Yttriumtrihalogeniden und Yttriumoxidhalogemden / Calorimetry of Yttrium Trihalides and Yttrium Oxyhalides
  2. Calorimetrie an Ammoniumyttriumhalogeniden / Calorimetry of Ammonium Yttrium Halides
  3. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalysen von Tetrahalogenooxalatoosmaten (IV), [OsX4(ox)]2-, X = Cl, Br, I / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of Tetrahalogenooxalatoosmates (IV), [OsX4(ox)]2-, X = Cl, Br, I
  4. The Phenomenon of Intramolecular Attractive S---O Interactions: Synthesis and Structure of (1,10-Phenanthroline)copper(II) Complexes with Isonitroso-(4-methylthiazol-2-yl)acetamide and Isonitroso-(4-methylthiazol-2-yl)-(benzothiazol-2-yl)methanide
  5. Direct Synthesis of Zinc and Nickel(II) Complexes with 1,4-Diazabicyclo[2.2.2]octane
  6. Crystal Structure of the Di-bromo-bis(2-dimethylaminoethanolato)(dimethylsulfoxide)-copper(II)-lead(II) Dimer Obtained by Direct Synthesis
  7. Unsymmetrische BN23--Ionen in den Strukturen von Ca2ClBN2 und Sr2ClBN2 / Unsymmetric BN23--Ions in the Structures of Ca2ClBN2 and Sr2ClBN2
  8. Bromierung von „Poly(1,4-diselenobenzol)“ / Bromination of “Poly(1,4-diselenobenzene)”
  9. Monoheteroarylborate [1] / Monoheteroarylborates [1]
  10. 1,3-Di-terf-butyl-6H-benzo[b]naphtho[1,2-d]pyran-6-thione, a Severely Helically Distorted Thionolactone-Bridged Biaryl
  11. Synthese und Struktur von Kalium-4,4-difluor-[1,3,2]dithiazetidinid-1,l,3,3-tetraoxid und Rubidium-4,4,5,5-tetrafluor-[1,3,2]dithiazolidinid-1,1,3,3-tetraoxid / Syntheses and Structure of Potassium-4,4-difluoro-[1,3,2]dithiazetidinide-1,1,3,3- tetraoxide and Rubidium-4,4,5,5-tetrafluoro-[ 1,3,2]dithiazolidinide-1,1,3,3-tetraoxide
  12. Synthese und Kristallstruktur eines Barium-Zink-Vanadyl-phosphats BaZn(VO)(PO4)2 mit [(VO)PO4]-Schichten / Synthesis and Crystal Structure of a Barium-Zinc-Vanadyl-Phosphate BaZn(VO)(PO4)2 Containing [(VO)PO4] Layers
  13. Einkernige und oxoverbrückte zweikernige Fe(III)-Komplexe von N-Alkyl-N,N-bis(2-pyridylmethyl)aminen / Mononuclear and Oxo-Bridged Binuclear Fe(III) Complexes of N-Alkyl-N,N-bis(2-pyridylmethyl)amines
  14. Diphenyl(1-pyridyl)phosphine Sulfide as a Ligand in Mono-and Binuclear Coinage Metal Complexes
  15. Röntgenstrukturuntersuchungen an Elpasolith-verwandten Hexacyanokomplexen [N(CH3)4]2A[M(CN)6] (A = Rb, Tl; M = Cr, Fe) / X-Ray Structure Investigations of Elpasolite Related Hexacyano Complexes [N(CH3)4]2A[M(CN)6] (A = Rb, Tl; M = Cr, Fe)
  16. Synthese und Kristallstruktur von Hexa(tert-butyl)bismocenium-tetrachloroaluminat / Synthesis and Crystal Structure of Hexa(tert-butyl)bismocenium Tetrachloroaluminate
  17. Über die Reaktionen von (CH3)4N+I-, (CH3)4N+ICl2-, (CH3)4N+ICl4- und (CH3)4N+Cl- mit Trifluormethylhypochlorit CF3OCl / The Reactions of (CH3)4N+I-, ( CH3)4N+ICl2-, (CH3)4N+ICl4- and (CH3)4N+Cl- with Trifluoromethylhypochlorite CF3OCl
  18. Hydrothermal Synthesis and Crystal Structure of the New Manganese(II) Thioantimonate(III), Mn(en)3Sb4S7
  19. Bondenolide, a New Diterpenoid from the Seeds of Caesalpinia bonduc
  20. Enzymatic Racemic Resolution of a Fluorinated Substrate and Syntheses of E and Z Alkenes as Precursors for Some Biologically Active Fluorohexoses
  21. Synthesis and Chiroptical Properties of Some N-(2-Chloro-7-cyclopropyl-4,7-dihydro-4-oxo-thieno[2,3-b]pyridine-5-carbonyl) L-α-Amino Esters
  22. Notizen: Synthesis of N,C,C-Trilithio-2,5-diallyl-pyrrole and its Solvent-Controlled Reactions with Electrophiles Notizen
  23. Notizen: A New Lithium Amide with Bulky Substituents -Molecular Structure of N-Lithio-N-trimethylsilyl-9-amino- 9-borabicyclo[3.3.1]nonane; Competition between N-Li and BN(pp)π Interactions
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