American Journal of Quantum Chemistry and Molecular Spectroscopy

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3-Sphere Approach on 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol

Received: 9 January 2024    Accepted: 20 January 2024    Published: 1 February 2024
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Abstract

The conformation of 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol 1, phase angles of the pseudorotation of five (C3) and six (C14) membered rings, was analyzed with dihedral angles θHnHn+1[deg] calculated only from vicinal coupling constants 3JHH[Hz] with 3-Sphere approach and VISION molecular models. The dimension space around the six and five membered ring are established based on hypersphere equations results from calculation of the dihedral angles from carbon chemical shift. Higher biological activity was observed to date at iminocyclitols having dihedral or vicinal angles calculated in 2D. Tetrahedral angles in close relationships with dihedral angles are calculated from carbon and / or proton chemical shift with manifold equations, conic and rectangle geometries. Equations for calculation of the tetrahedral angles φCn[deg] only from vicinal coupling constant 3JHnHn+1[deg] or from chemical shift δCn[ppm] are analyzed for five and established for six membered ring, resulting general rules for calculation of tetrahedral angles. Conic as manifold in case of six membered ring enable calculation of dihedral angle θHnHn+1[deg] from tetrahedral angle φCn[deg] starting with tetrahedral angle on unit, and in case of five membered ring based on opposite relationship between dihedral and tetrahedral (sin versus tan function), unit start with dihedral angles. Rectangle as manifold enable calculation for both the tetrahedral angle from dihedral angle starting with dihedral angle on unit, for six membered ring using two or three units with three sets angles and in case of five membered ring only one unit with seven set angles. The bond distances lCnCn+1 [A0] of five and six membered ring are calculated from 3-Sphere-dihedral angles θHnHn+1[deg].

DOI 10.11648/ajqcms.20240801.11
Published in American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 8, Issue 1, June 2024)
Page(s) 1-12
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

3-Sphere-Dihedral Angles, Phase Angle of the Pseudorotation, Tetrahedral Angles, Bond Distances

References
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    Moriarty, R. M., Mitan, C., Bartha, E., Filip, P., Naithani, R., et al. (2024). 3-Sphere Approach on 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol. American Journal of Quantum Chemistry and Molecular Spectroscopy, 8(1), 1-12. https://doi.org/10.11648/ajqcms.20240801.11

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    Moriarty, R. M.; Mitan, C.; Bartha, E.; Filip, P.; Naithani, R., et al. 3-Sphere Approach on 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol. Am. J. Quantum Chem. Mol. Spectrosc. 2024, 8(1), 1-12. doi: 10.11648/ajqcms.20240801.11

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    AMA Style

    Moriarty RM, Mitan C, Bartha E, Filip P, Naithani R, et al. 3-Sphere Approach on 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol. Am J Quantum Chem Mol Spectrosc. 2024;8(1):1-12. doi: 10.11648/ajqcms.20240801.11

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  • @article{10.11648/ajqcms.20240801.11,
      author = {Robert Michael Moriarty and Carmen-Irena Mitan and Emerich Bartha and Petru Filip and Rajesh Naithani and Timothy Block},
      title = {3-Sphere Approach on 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol},
      journal = {American Journal of Quantum Chemistry and Molecular Spectroscopy},
      volume = {8},
      number = {1},
      pages = {1-12},
      doi = {10.11648/ajqcms.20240801.11},
      url = {https://doi.org/10.11648/ajqcms.20240801.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.ajqcms.20240801.11},
      abstract = {The conformation of 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol 1, phase angles of the pseudorotation of five (C3) and six (C14) membered rings, was analyzed with dihedral angles θHnHn+1[deg] calculated only from vicinal coupling constants 3JHH[Hz] with 3-Sphere approach and VISION molecular models. The dimension space around the six and five membered ring are established based on hypersphere equations results from calculation of the dihedral angles from carbon chemical shift. Higher biological activity was observed to date at iminocyclitols having dihedral or vicinal angles calculated in 2D. Tetrahedral angles in close relationships with dihedral angles are calculated from carbon and / or proton chemical shift with manifold equations, conic and rectangle geometries. Equations for calculation of the tetrahedral angles φCn[deg] only from vicinal coupling constant 3JHnHn+1[deg] or from chemical shift δCn[ppm] are analyzed for five and established for six membered ring, resulting general rules for calculation of tetrahedral angles. Conic as manifold in case of six membered ring enable calculation of dihedral angle θHnHn+1[deg] from tetrahedral angle φCn[deg] starting with tetrahedral angle on unit, and in case of five membered ring based on opposite relationship between dihedral and tetrahedral (sin versus tan function), unit start with dihedral angles. Rectangle as manifold enable calculation for both the tetrahedral angle from dihedral angle starting with dihedral angle on unit, for six membered ring using two or three units with three sets angles and in case of five membered ring only one unit with seven set angles. The bond distances lCnCn+1 [A0] of five and six membered ring are calculated from 3-Sphere-dihedral angles θHnHn+1[deg].
    },
     year = {2024}
    }
    

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    T1  - 3-Sphere Approach on 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol
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    AU  - Carmen-Irena Mitan
    AU  - Emerich Bartha
    AU  - Petru Filip
    AU  - Rajesh Naithani
    AU  - Timothy Block
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    N1  - https://doi.org/10.11648/ajqcms.20240801.11
    DO  - 10.11648/ajqcms.20240801.11
    T2  - American Journal of Quantum Chemistry and Molecular Spectroscopy
    JF  - American Journal of Quantum Chemistry and Molecular Spectroscopy
    JO  - American Journal of Quantum Chemistry and Molecular Spectroscopy
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    PB  - Science Publishing Group
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    AB  - The conformation of 9-O-(10,11-di-O-benzyl-12,14-O-benzylidene-α-D-galactopyranosyl)-1-butyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-L-ribitol 1, phase angles of the pseudorotation of five (C3) and six (C14) membered rings, was analyzed with dihedral angles θHnHn+1[deg] calculated only from vicinal coupling constants 3JHH[Hz] with 3-Sphere approach and VISION molecular models. The dimension space around the six and five membered ring are established based on hypersphere equations results from calculation of the dihedral angles from carbon chemical shift. Higher biological activity was observed to date at iminocyclitols having dihedral or vicinal angles calculated in 2D. Tetrahedral angles in close relationships with dihedral angles are calculated from carbon and / or proton chemical shift with manifold equations, conic and rectangle geometries. Equations for calculation of the tetrahedral angles φCn[deg] only from vicinal coupling constant 3JHnHn+1[deg] or from chemical shift δCn[ppm] are analyzed for five and established for six membered ring, resulting general rules for calculation of tetrahedral angles. Conic as manifold in case of six membered ring enable calculation of dihedral angle θHnHn+1[deg] from tetrahedral angle φCn[deg] starting with tetrahedral angle on unit, and in case of five membered ring based on opposite relationship between dihedral and tetrahedral (sin versus tan function), unit start with dihedral angles. Rectangle as manifold enable calculation for both the tetrahedral angle from dihedral angle starting with dihedral angle on unit, for six membered ring using two or three units with three sets angles and in case of five membered ring only one unit with seven set angles. The bond distances lCnCn+1 [A0] of five and six membered ring are calculated from 3-Sphere-dihedral angles θHnHn+1[deg].
    
    VL  - 8
    IS  - 1
    ER  - 

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Author Information
  • Department of Chemistry, University of Illinois at Chicago, Chicago, US

  • Department of Chemistry, University of Illinois at Chicago, Chicago, US; Department of Chemistry, “C.D. Nenitescu”, Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

  • Department of Chemistry, “C.D. Nenitescu”, Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

  • Department of Chemistry, “C.D. Nenitescu”, Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

  • Department of Chemistry, University of Illinois at Chicago, Chicago, US

  • Drexel Institute for Biotechnology and Virology Research, College of Medicine, Drexel University, Doylestown, US

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