3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data

Carmen-Irena Mitan; Emerich Bartha; Petru Filip; Valeriu Dragutan; Ileana Dragutan; Calin Deleanu; Constantin Draghici; Miron-Teodor Caproiu; Robert Michael Moriarty

doi:doi:10.11648/j.sjc.20261401.11

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3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data

Carmen-Irena Mitan^*

, Emerich Bartha, Petru Filip

, Valeriu Dragutan, Ileana Dragutan, Calin Deleanu

, Constantin Draghici, Miron-Teodor Caproiu, Robert Michael Moriarty

Published in Science Journal of Chemistry (Volume 14, Issue 1)

Received: 22 December 2025 Accepted: 6 January 2026 Published: 2 February 2026

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Abstract

3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θ_HnHn+1 [deg] – tetrahedral φ_Cn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling constant ³J_HH [Hz] and carbon chemical shift δ_C [ppm]. This approach gave for 1-α-methyl-1,4-imino-1,4-dideoxy-D-ribitol 2 two conformers E₃ and ³T₂ having different dihedral θ_HnHn+1 [deg] and tetrahedral φ_Cn [deg] angles with same vicinal angles ϕ [deg]. Notably, phase angle of pseudorotation P [deg] placed the conformations on the south side for D-ribitols 1 - 3 and on the north side for L-ribitol 4, excepting trifluoroacetate salt of L-ribitol 5. The wave character of NMR data introduced few homotopic switches, the transformation from torus to inverse of torus, the relationship between angles of set A and set B, the transformation from Planck constants h to h-bar, along with the transformation from Joule to Calorie (J 4.1868 ⇆ J^-1 0.238). Two methods for calculation of tetrahedral angles φ_Cn [deg], energy-graph and Euler conic with two ways for representing the angles, polyhedron and unit models are analyzed. The conformational parameters, phase angle of the pseudorotation P [deg] established with VISION molecular model and exocyclic 3-Sphere dihedral angles θ_HnHn+1 [deg] relative to endocyclic torsional angles θ_n,n₊₁ [deg] from Altona-Sundaralingan model have been evaluated. In addition, the corresponding angle of deviation from planarity θ_m [deg] has been determined.

Published in	Science Journal of Chemistry (Volume 14, Issue 1)
DOI	10.11648/j.sjc.20261401.11
Page(s)	1-11
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), 2026. Published by Science Publishing Group

Keywords

3-Sphere, Dihedral Angles, Vicinal Angles, Vicinal Coupling Constant, Tetrahedral Angles, Phase Angle of the Pseudorotation, Angle of Deviation from Planarity, Conformational Analysis, Iminocyclitols

References

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[2]	C.-I. Mitan, E. Bartha, P. Filip, C. Draghici, M.-T. Caproiu, R. M. Moriarty, ACS Spring, San Diego march 23 - 27, 2025 CARB 623, https://doi.org/10.1021/scimeetings.5c11051
[3]	C.-I. Mitan, P. Filip, E. Bartha, C. Draghici, M.-T. Caproiu, R. M. Moriarty, ACS San Diego march 23 - 27, 2025 Sci-Mix CARB - ANYL 632, https://doi.org/10.1021/scimeetings.5c11052
[4]	C. Altona, M. Sundaralingam, Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using concept of pseudorotation, J. Am. Chem. Soc. 1972, 94, 8205; https://doi.org/10.1021/ja00778a043
[5]	B. Coxon, Chapter 3 Developments in the Karplus equation as they relate to the NMR coupling constants of carbohydrates, Adv. Carb. Chem. Biochem. 2009, 62, 17; https://doi.org/10.1016/50065-2318(09)00003-1
[6]	J. B. Houseknecht, C. Altona, C. M. Hadad, T. Lawary, Conformational analysis of furanose rings with PSEUROT: Parametrization for rings possessing the arabino, lyxo, ribo, and xylo stereochemistry and application to arabinofuranosides, J. Org. Chem. 2002, 67, 4647; https://doi.org/10.1021/jo025635q
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[9]	C.-I. Mitan, E. Bartha, P. Filip, C. Draghici, M. T. Caproiu, R. M. Moriarty, Dihedral angles calculated with 3-sphere approach as integer in conformational analysis on D-, L- ribitol series, Rev. Roum. Chim. 2022, 66(21), 941, https://doi.org/10.33224/rrch.2021.66.12.07
[10]	C. Altona, M. Sundaralingam, Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constant, J. Am. Chem. Soc. 1972, 2333; https://doi.org/10.1021/ja00778a043
[11]	VISION molecular models, darling Models, Inc. P. O. Box 1818, Stow, Ohio 44224 U.S.A.
[12]	R. M. Moriarty, C. I. Mitan, N. Branza-Nichita, K. R. Phares, D. Parrish, exo-Imino to endo-iminocyclitol rearrangement. A general route to five membered antiviral azasugars, Org. Lett. 2006, 8, 3465; https://doi.org/10.1021/ol061071r
[13]	E. Bartha, C.-I. Mitan, C. Draghici, M.-T. Caproiu, P. Filip, L. Tarko, R. M. Moriarty, Program for prediction dihedral angle from vicinal coupling constant with 3-sphere approach, Rev. Roum. Chim. 2021, 66(2), 179; https://doi.org/10.33224/rrch.2021.66.2.08
[14]	C.-I. Mitan, E. Bartha, P. Filip, C. Draghici, M. T. Caproiu, R. M. Moriarty, Manifold inversion on prediction dihedral angles from vicinal coupling constant with 3-Sphere approach, Rev. Roum. Chim. 2023, 68(3-4), 185; https://doi.org/10.33224/rrch.2023.68.3-4.08
[15]	E. Bartha, C.-I. Mitan, P. Filip, 3-Sphere torsional angles and six membered ring conformation, Am. J. Quant. Chem. and Mol. Spec. 2023, 7(1), 9; https://doi.org/10.11648/j.ajqcms.20230701.12
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[17]	C.-I. Mitan, E. Bartha, C. Draghici, M.-T. Caproiu, P. Filip, R. M. Moriarty, Tetrahedral angles of five membered ring iminocyclitols with ribitol stereochemistry beyond the dihedral angles, Rev. Roum. Chim. 2022, 67(3), 165; https://doi.org/10.33224/rrch.2022.67.3.04
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[19]	Mathematical Institute, University of Oxford, Homotopy, http://people.maths.ox.ac.uk/nanda/cat/lecture02Hmotopy.pdf
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[21]	E. Westhof, M. Sundaralingam, A method for the analysis of puckering disorder in five - membered rings: the relative mobilities of furanose and proline rings and their effects on polynucleotide and polypeptide backbone flexibility, J. Am. Chem. Soc. 1983, 105, 970; https://doi.org/10.1021/ja00342a054
[22]	M. J. Frisch et. al., Gausian09W C. 01, Gaussian Inc., 340 Quinnipioc St Bldg 40, Wallingford, CT 06492 USA; HYPERLINK " http://www.gaussian.com" www.gaussian.com

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APA Style

Mitan, C., Bartha, E., Filip, P., Dragutan, V., Dragutan, I., et al. (2026). 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data. Science Journal of Chemistry, 14(1), 1-11. https://doi.org/10.11648/j.sjc.20261401.11

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ACS Style

Mitan, C.; Bartha, E.; Filip, P.; Dragutan, V.; Dragutan, I., et al. 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data. Sci. J. Chem. 2026, 14(1), 1-11. doi: 10.11648/j.sjc.20261401.11

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AMA Style

Mitan C, Bartha E, Filip P, Dragutan V, Dragutan I, et al. 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data. Sci J Chem. 2026;14(1):1-11. doi: 10.11648/j.sjc.20261401.11

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@article{10.11648/j.sjc.20261401.11,
  author = {Carmen-Irena Mitan and Emerich Bartha and Petru Filip and Valeriu Dragutan and Ileana Dragutan and Calin Deleanu and Constantin Draghici and Miron-Teodor Caproiu and Robert Michael Moriarty},
  title = {3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data},
  journal = {Science Journal of Chemistry},
  volume = {14},
  number = {1},
  pages = {1-11},
  doi = {10.11648/j.sjc.20261401.11},
  url = {https://doi.org/10.11648/j.sjc.20261401.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20261401.11},
  abstract = {3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θHnHn+1 [deg] – tetrahedral φCn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling constant 3JHH [Hz] and carbon chemical shift δC [ppm]. This approach gave for 1-α-methyl-1,4-imino-1,4-dideoxy-D-ribitol 2 two conformers E3 and 3T2 having different dihedral θHnHn+1 [deg] and tetrahedral φCn [deg] angles with same vicinal angles ϕ [deg]. Notably, phase angle of pseudorotation P [deg] placed the conformations on the south side for D-ribitols 1 - 3 and on the north side for L-ribitol 4, excepting trifluoroacetate salt of L-ribitol 5. The wave character of NMR data introduced few homotopic switches, the transformation from torus to inverse of torus, the relationship between angles of set A and set B, the transformation from Planck constants h to h-bar, along with the transformation from Joule to Calorie (J 4.1868 ⇆ J-1 0.238). Two methods for calculation of tetrahedral angles φCn [deg], energy-graph and Euler conic with two ways for representing the angles, polyhedron and unit models are analyzed. The conformational parameters, phase angle of the pseudorotation P [deg] established with VISION molecular model and exocyclic 3-Sphere dihedral angles θHnHn+1 [deg] relative to endocyclic torsional angles θn,n+1 [deg] from Altona-Sundaralingan model have been evaluated. In addition, the corresponding angle of deviation from planarity θm [deg] has been determined.},
 year = {2026}
}

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TY  - JOUR
T1  - 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data
AU  - Carmen-Irena Mitan
AU  - Emerich Bartha
AU  - Petru Filip
AU  - Valeriu Dragutan
AU  - Ileana Dragutan
AU  - Calin Deleanu
AU  - Constantin Draghici
AU  - Miron-Teodor Caproiu
AU  - Robert Michael Moriarty
Y1  - 2026/02/02
PY  - 2026
N1  - https://doi.org/10.11648/j.sjc.20261401.11
DO  - 10.11648/j.sjc.20261401.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 1
EP  - 11
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20261401.11
AB  - 3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θHnHn+1 [deg] – tetrahedral φCn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling constant 3JHH [Hz] and carbon chemical shift δC [ppm]. This approach gave for 1-α-methyl-1,4-imino-1,4-dideoxy-D-ribitol 2 two conformers E3 and 3T2 having different dihedral θHnHn+1 [deg] and tetrahedral φCn [deg] angles with same vicinal angles ϕ [deg]. Notably, phase angle of pseudorotation P [deg] placed the conformations on the south side for D-ribitols 1 - 3 and on the north side for L-ribitol 4, excepting trifluoroacetate salt of L-ribitol 5. The wave character of NMR data introduced few homotopic switches, the transformation from torus to inverse of torus, the relationship between angles of set A and set B, the transformation from Planck constants h to h-bar, along with the transformation from Joule to Calorie (J 4.1868 ⇆ J-1 0.238). Two methods for calculation of tetrahedral angles φCn [deg], energy-graph and Euler conic with two ways for representing the angles, polyhedron and unit models are analyzed. The conformational parameters, phase angle of the pseudorotation P [deg] established with VISION molecular model and exocyclic 3-Sphere dihedral angles θHnHn+1 [deg] relative to endocyclic torsional angles θn,n+1 [deg] from Altona-Sundaralingan model have been evaluated. In addition, the corresponding angle of deviation from planarity θm [deg] has been determined.
VL  - 14
IS  - 1
ER  -

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Author Information

Carmen-Irena Mitan

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

Contact Email

http://orcid.org/0000-0002-4790-3122
Emerich Bartha

Department of Organic Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry of Roumanian Academy, Bucharest, Romania
Petru Filip

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

Contact Email

http://orcid.org/0000-0003-2076-7244
Valeriu Dragutan

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

Contact Email
Ileana Dragutan

Department of Organic Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry of Roumanian Academy, Bucharest, Romania
Calin Deleanu

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

http://orcid.org/0000-0001-8206-5227
Constantin Draghici

Department of Organic Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry of Roumanian Academy, Bucharest, Romania
Miron-Teodor Caproiu

Department of Organic Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry of Roumanian Academy, Bucharest, Romania
Robert Michael Moriarty

Department of Chemistry, University of Illinois at Chicago, Chicago, USA

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APA Style

Mitan, C., Bartha, E., Filip, P., Dragutan, V., Dragutan, I., et al. (2026). 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data. Science Journal of Chemistry, 14(1), 1-11. https://doi.org/10.11648/j.sjc.20261401.11

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ACS Style

Mitan, C.; Bartha, E.; Filip, P.; Dragutan, V.; Dragutan, I., et al. 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data. Sci. J. Chem. 2026, 14(1), 1-11. doi: 10.11648/j.sjc.20261401.11

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AMA Style

Mitan C, Bartha E, Filip P, Dragutan V, Dragutan I, et al. 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data. Sci J Chem. 2026;14(1):1-11. doi: 10.11648/j.sjc.20261401.11

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@article{10.11648/j.sjc.20261401.11,
  author = {Carmen-Irena Mitan and Emerich Bartha and Petru Filip and Valeriu Dragutan and Ileana Dragutan and Calin Deleanu and Constantin Draghici and Miron-Teodor Caproiu and Robert Michael Moriarty},
  title = {3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data},
  journal = {Science Journal of Chemistry},
  volume = {14},
  number = {1},
  pages = {1-11},
  doi = {10.11648/j.sjc.20261401.11},
  url = {https://doi.org/10.11648/j.sjc.20261401.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20261401.11},
  abstract = {3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θHnHn+1 [deg] – tetrahedral φCn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling constant 3JHH [Hz] and carbon chemical shift δC [ppm]. This approach gave for 1-α-methyl-1,4-imino-1,4-dideoxy-D-ribitol 2 two conformers E3 and 3T2 having different dihedral θHnHn+1 [deg] and tetrahedral φCn [deg] angles with same vicinal angles ϕ [deg]. Notably, phase angle of pseudorotation P [deg] placed the conformations on the south side for D-ribitols 1 - 3 and on the north side for L-ribitol 4, excepting trifluoroacetate salt of L-ribitol 5. The wave character of NMR data introduced few homotopic switches, the transformation from torus to inverse of torus, the relationship between angles of set A and set B, the transformation from Planck constants h to h-bar, along with the transformation from Joule to Calorie (J 4.1868 ⇆ J-1 0.238). Two methods for calculation of tetrahedral angles φCn [deg], energy-graph and Euler conic with two ways for representing the angles, polyhedron and unit models are analyzed. The conformational parameters, phase angle of the pseudorotation P [deg] established with VISION molecular model and exocyclic 3-Sphere dihedral angles θHnHn+1 [deg] relative to endocyclic torsional angles θn,n+1 [deg] from Altona-Sundaralingan model have been evaluated. In addition, the corresponding angle of deviation from planarity θm [deg] has been determined.},
 year = {2026}
}

Copy | Download

TY  - JOUR
T1  - 3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data
AU  - Carmen-Irena Mitan
AU  - Emerich Bartha
AU  - Petru Filip
AU  - Valeriu Dragutan
AU  - Ileana Dragutan
AU  - Calin Deleanu
AU  - Constantin Draghici
AU  - Miron-Teodor Caproiu
AU  - Robert Michael Moriarty
Y1  - 2026/02/02
PY  - 2026
N1  - https://doi.org/10.11648/j.sjc.20261401.11
DO  - 10.11648/j.sjc.20261401.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 1
EP  - 11
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20261401.11
AB  - 3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θHnHn+1 [deg] – tetrahedral φCn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling constant 3JHH [Hz] and carbon chemical shift δC [ppm]. This approach gave for 1-α-methyl-1,4-imino-1,4-dideoxy-D-ribitol 2 two conformers E3 and 3T2 having different dihedral θHnHn+1 [deg] and tetrahedral φCn [deg] angles with same vicinal angles ϕ [deg]. Notably, phase angle of pseudorotation P [deg] placed the conformations on the south side for D-ribitols 1 - 3 and on the north side for L-ribitol 4, excepting trifluoroacetate salt of L-ribitol 5. The wave character of NMR data introduced few homotopic switches, the transformation from torus to inverse of torus, the relationship between angles of set A and set B, the transformation from Planck constants h to h-bar, along with the transformation from Joule to Calorie (J 4.1868 ⇆ J-1 0.238). Two methods for calculation of tetrahedral angles φCn [deg], energy-graph and Euler conic with two ways for representing the angles, polyhedron and unit models are analyzed. The conformational parameters, phase angle of the pseudorotation P [deg] established with VISION molecular model and exocyclic 3-Sphere dihedral angles θHnHn+1 [deg] relative to endocyclic torsional angles θn,n+1 [deg] from Altona-Sundaralingan model have been evaluated. In addition, the corresponding angle of deviation from planarity θm [deg] has been determined.
VL  - 14
IS  - 1
ER  -

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