Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach

Carmen-Irena Mitan; Emeric Bartha; Anca Hirtopeanu; Carmen Stavarache; Constantin Draghici; Miron Teodor Caproiu; Maria Maganu; Petru Filip

doi:doi:10.11648/j.ajqcms.20230701.11

Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach

Carmen-Irena Mitan, Emeric Bartha, Anca Hirtopeanu, Carmen Stavarache, Constantin Draghici, Miron Teodor Caproiu, Maria Maganu, Petru Filip

Published in American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 7, Issue 1)

Received: 7 March 2023 Accepted: 27 March 2023 Published: 11 April 2023

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Abstract

Configurational and conformational analysis with 3-Sphere approach on selective iodination of α, β-methyl D-ribofuranose (2-α:2-β) with iodotriphenilphosphonium iodide complex [Ph₃P⁺I]I^- generated in situ, under RT, reflux, microwave and sonochemistry. Introduction of the unit and hypersphere trigonometric equations, under Hopf fibration and Lie algebra theories, on Lambert-Wu methods enable calculation of the dihedral angles from NMR data (¹³C chemical shift, vicinal coupling constant ³J_HH[Hz]) and the ratio of anomers. The conformation/configuration at anomeric position is cis: trans with axial:axial 3-α:3-β (³J_H1H2 3 or 4.5:0[Hz]) or equatorial:axial 3-α:3-β (³J_H1H2 6 or 4.5:0[Hz]) as state based on dihedral angles θ_H1H2[deg], recorded carbon chemical shift δ_Cn[deg] and VISION molecular models. The conformation of 3-β anomer is ³E, and in case of 3-α anomer ₃E on Altona’s map, the last having the succession of sign (+, -, -) with θ_H3H4^α trans-ee, or alternatively ³₂T conformation having the succession of sign (-, +, -) with θ_H3H4^α trans-aa. An equilibrium between ₃E^α and ³₂T^α was confirmed by ³J_H1H2 of 4.5[Hz], i.e. negative θ_H1H2^α with ³₂T and equatorial OCH₃, or positive θ_H1H2^α with ₃E and axial OCH₃. The APT experiment (attached proton test) demonstrated the formation of tetrahydro 2H-pyran-2-ol as side product after selective iodination of methyl 5-deoxy-β-D-ribofuranoside 2-β.

Published in	American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 7, Issue 1)
DOI	10.11648/j.ajqcms.20230701.11
Page(s)	1-8
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), 2023. Published by Science Publishing Group

Keywords

3-Sphere, Dihedral Angles, Configuration, Conformation, Selective Iodination

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Carmen-Irena Mitan, Emeric Bartha, Anca Hirtopeanu, Carmen Stavarache, Constantin Draghici, et al. (2023). Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach. American Journal of Quantum Chemistry and Molecular Spectroscopy, 7(1), 1-8. https://doi.org/10.11648/j.ajqcms.20230701.11

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ACS Style

Carmen-Irena Mitan; Emeric Bartha; Anca Hirtopeanu; Carmen Stavarache; Constantin Draghici, et al. Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach. Am. J. Quantum Chem. Mol. Spectrosc. 2023, 7(1), 1-8. doi: 10.11648/j.ajqcms.20230701.11

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AMA Style

Carmen-Irena Mitan, Emeric Bartha, Anca Hirtopeanu, Carmen Stavarache, Constantin Draghici, et al. Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach. Am J Quantum Chem Mol Spectrosc. 2023;7(1):1-8. doi: 10.11648/j.ajqcms.20230701.11

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@article{10.11648/j.ajqcms.20230701.11,
  author = {Carmen-Irena Mitan and Emeric Bartha and Anca Hirtopeanu and Carmen Stavarache and Constantin Draghici and Miron Teodor Caproiu and Maria Maganu and Petru Filip},
  title = {Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach},
  journal = {American Journal of Quantum Chemistry and Molecular Spectroscopy},
  volume = {7},
  number = {1},
  pages = {1-8},
  doi = {10.11648/j.ajqcms.20230701.11},
  url = {https://doi.org/10.11648/j.ajqcms.20230701.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajqcms.20230701.11},
  abstract = {Configurational and conformational analysis with 3-Sphere approach on selective iodination of α, β-methyl D-ribofuranose (2-α:2-β) with iodotriphenilphosphonium iodide complex [Ph3P+I]I- generated in situ, under RT, reflux, microwave and sonochemistry. Introduction of the unit and hypersphere trigonometric equations, under Hopf fibration and Lie algebra theories, on Lambert-Wu methods enable calculation of the dihedral angles from NMR data (13C chemical shift, vicinal coupling constant 3JHH[Hz]) and the ratio of anomers. The conformation/configuration at anomeric position is cis: trans with axial:axial 3-α:3-β (3JH1H2 3 or 4.5:0[Hz]) or equatorial:axial 3-α:3-β (3JH1H2 6 or 4.5:0[Hz]) as state based on dihedral angles θH1H2[deg], recorded carbon chemical shift δCn[deg] and VISION molecular models. The conformation of 3-β anomer is 3E, and in case of 3-α anomer 3E on Altona’s map, the last having the succession of sign (+, -, -) with θH3H4α trans-ee, or alternatively 32T conformation having the succession of sign (-, +, -) with θH3H4α trans-aa. An equilibrium between 3E α and 32T α was confirmed by 3JH1H2 of 4.5[Hz], i.e. negative θH1H2α with 32T and equatorial OCH3, or positive θH1H2α with 3E and axial OCH3. The APT experiment (attached proton test) demonstrated the formation of tetrahydro 2H-pyran-2-ol as side product after selective iodination of methyl 5-deoxy-β-D-ribofuranoside 2-β.},
 year = {2023}
}

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TY  - JOUR
T1  - Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach
AU  - Carmen-Irena Mitan
AU  - Emeric Bartha
AU  - Anca Hirtopeanu
AU  - Carmen Stavarache
AU  - Constantin Draghici
AU  - Miron Teodor Caproiu
AU  - Maria Maganu
AU  - Petru Filip
Y1  - 2023/04/11
PY  - 2023
N1  - https://doi.org/10.11648/j.ajqcms.20230701.11
DO  - 10.11648/j.ajqcms.20230701.11
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
SP  - 1
EP  - 8
PB  - Science Publishing Group
SN  - 2994-7308
UR  - https://doi.org/10.11648/j.ajqcms.20230701.11
AB  - Configurational and conformational analysis with 3-Sphere approach on selective iodination of α, β-methyl D-ribofuranose (2-α:2-β) with iodotriphenilphosphonium iodide complex [Ph3P+I]I- generated in situ, under RT, reflux, microwave and sonochemistry. Introduction of the unit and hypersphere trigonometric equations, under Hopf fibration and Lie algebra theories, on Lambert-Wu methods enable calculation of the dihedral angles from NMR data (13C chemical shift, vicinal coupling constant 3JHH[Hz]) and the ratio of anomers. The conformation/configuration at anomeric position is cis: trans with axial:axial 3-α:3-β (3JH1H2 3 or 4.5:0[Hz]) or equatorial:axial 3-α:3-β (3JH1H2 6 or 4.5:0[Hz]) as state based on dihedral angles θH1H2[deg], recorded carbon chemical shift δCn[deg] and VISION molecular models. The conformation of 3-β anomer is 3E, and in case of 3-α anomer 3E on Altona’s map, the last having the succession of sign (+, -, -) with θH3H4α trans-ee, or alternatively 32T conformation having the succession of sign (-, +, -) with θH3H4α trans-aa. An equilibrium between 3E α and 32T α was confirmed by 3JH1H2 of 4.5[Hz], i.e. negative θH1H2α with 32T and equatorial OCH3, or positive θH1H2α with 3E and axial OCH3. The APT experiment (attached proton test) demonstrated the formation of tetrahydro 2H-pyran-2-ol as side product after selective iodination of methyl 5-deoxy-β-D-ribofuranoside 2-β.
VL  - 7
IS  - 1
ER  -

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Author Information

Carmen-Irena Mitan

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Emeric Bartha

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Anca Hirtopeanu

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Carmen Stavarache

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Constantin Draghici

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Miron Teodor Caproiu

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Maria Maganu

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania
Petru Filip

“C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, Bucharest, Romania

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Carmen-Irena Mitan, Emeric Bartha, Anca Hirtopeanu, Carmen Stavarache, Constantin Draghici, et al. (2023). Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach. American Journal of Quantum Chemistry and Molecular Spectroscopy, 7(1), 1-8. https://doi.org/10.11648/j.ajqcms.20230701.11

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ACS Style

Carmen-Irena Mitan; Emeric Bartha; Anca Hirtopeanu; Carmen Stavarache; Constantin Draghici, et al. Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach. Am. J. Quantum Chem. Mol. Spectrosc. 2023, 7(1), 1-8. doi: 10.11648/j.ajqcms.20230701.11

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AMA Style

Carmen-Irena Mitan, Emeric Bartha, Anca Hirtopeanu, Carmen Stavarache, Constantin Draghici, et al. Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach. Am J Quantum Chem Mol Spectrosc. 2023;7(1):1-8. doi: 10.11648/j.ajqcms.20230701.11

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@article{10.11648/j.ajqcms.20230701.11,
  author = {Carmen-Irena Mitan and Emeric Bartha and Anca Hirtopeanu and Carmen Stavarache and Constantin Draghici and Miron Teodor Caproiu and Maria Maganu and Petru Filip},
  title = {Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach},
  journal = {American Journal of Quantum Chemistry and Molecular Spectroscopy},
  volume = {7},
  number = {1},
  pages = {1-8},
  doi = {10.11648/j.ajqcms.20230701.11},
  url = {https://doi.org/10.11648/j.ajqcms.20230701.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajqcms.20230701.11},
  abstract = {Configurational and conformational analysis with 3-Sphere approach on selective iodination of α, β-methyl D-ribofuranose (2-α:2-β) with iodotriphenilphosphonium iodide complex [Ph3P+I]I- generated in situ, under RT, reflux, microwave and sonochemistry. Introduction of the unit and hypersphere trigonometric equations, under Hopf fibration and Lie algebra theories, on Lambert-Wu methods enable calculation of the dihedral angles from NMR data (13C chemical shift, vicinal coupling constant 3JHH[Hz]) and the ratio of anomers. The conformation/configuration at anomeric position is cis: trans with axial:axial 3-α:3-β (3JH1H2 3 or 4.5:0[Hz]) or equatorial:axial 3-α:3-β (3JH1H2 6 or 4.5:0[Hz]) as state based on dihedral angles θH1H2[deg], recorded carbon chemical shift δCn[deg] and VISION molecular models. The conformation of 3-β anomer is 3E, and in case of 3-α anomer 3E on Altona’s map, the last having the succession of sign (+, -, -) with θH3H4α trans-ee, or alternatively 32T conformation having the succession of sign (-, +, -) with θH3H4α trans-aa. An equilibrium between 3E α and 32T α was confirmed by 3JH1H2 of 4.5[Hz], i.e. negative θH1H2α with 32T and equatorial OCH3, or positive θH1H2α with 3E and axial OCH3. The APT experiment (attached proton test) demonstrated the formation of tetrahydro 2H-pyran-2-ol as side product after selective iodination of methyl 5-deoxy-β-D-ribofuranoside 2-β.},
 year = {2023}
}

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TY  - JOUR
T1  - Configurational and Conformational Analysis of 5-deoxy-5-iodo-α,β-D-ribose with 3-Sphere Approach
AU  - Carmen-Irena Mitan
AU  - Emeric Bartha
AU  - Anca Hirtopeanu
AU  - Carmen Stavarache
AU  - Constantin Draghici
AU  - Miron Teodor Caproiu
AU  - Maria Maganu
AU  - Petru Filip
Y1  - 2023/04/11
PY  - 2023
N1  - https://doi.org/10.11648/j.ajqcms.20230701.11
DO  - 10.11648/j.ajqcms.20230701.11
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
SP  - 1
EP  - 8
PB  - Science Publishing Group
SN  - 2994-7308
UR  - https://doi.org/10.11648/j.ajqcms.20230701.11
AB  - Configurational and conformational analysis with 3-Sphere approach on selective iodination of α, β-methyl D-ribofuranose (2-α:2-β) with iodotriphenilphosphonium iodide complex [Ph3P+I]I- generated in situ, under RT, reflux, microwave and sonochemistry. Introduction of the unit and hypersphere trigonometric equations, under Hopf fibration and Lie algebra theories, on Lambert-Wu methods enable calculation of the dihedral angles from NMR data (13C chemical shift, vicinal coupling constant 3JHH[Hz]) and the ratio of anomers. The conformation/configuration at anomeric position is cis: trans with axial:axial 3-α:3-β (3JH1H2 3 or 4.5:0[Hz]) or equatorial:axial 3-α:3-β (3JH1H2 6 or 4.5:0[Hz]) as state based on dihedral angles θH1H2[deg], recorded carbon chemical shift δCn[deg] and VISION molecular models. The conformation of 3-β anomer is 3E, and in case of 3-α anomer 3E on Altona’s map, the last having the succession of sign (+, -, -) with θH3H4α trans-ee, or alternatively 32T conformation having the succession of sign (-, +, -) with θH3H4α trans-aa. An equilibrium between 3E α and 32T α was confirmed by 3JH1H2 of 4.5[Hz], i.e. negative θH1H2α with 32T and equatorial OCH3, or positive θH1H2α with 3E and axial OCH3. The APT experiment (attached proton test) demonstrated the formation of tetrahydro 2H-pyran-2-ol as side product after selective iodination of methyl 5-deoxy-β-D-ribofuranoside 2-β.
VL  - 7
IS  - 1
ER  -

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