View in EDS

Computational NMR of Carbohydrates. 2. Allopyranoses: Theoretical Conformational Analysis and NMR Calculations.

Saved in:
Bibliographic Details
Title: Computational NMR of Carbohydrates. 2. Allopyranoses: Theoretical Conformational Analysis and NMR Calculations.
Authors: Fedorov, Sergei V.1 (AUTHOR), Semenov, Valentin A.1 (AUTHOR), Krivdin, Leonid B.1 (AUTHOR) krivdin55@gmail.com
Source: Journal of Physical Organic Chemistry. May2026, Vol. 39 Issue 5, p1-13. 13p.
Subjects: Carbohydrates, Conformational analysis, Molecular dynamics, Density functional theory, Nuclear magnetic resonance, Nuclear magnetic resonance spectroscopy, Pyranoses
Abstract: Allose, an aldohexose sugar, is a rare natural monosaccharide that occurs in nature in the form of a 6‐O‐cinnamyl glycoside in the leaves of the African shrub Protea rubropilosa. It differs from glucose in the orientation of the hydroxyl group at the C‐3 position, being thus the C‐3 substituted epimer of glucopyranose. In this paper, a detailed theoretical modeling of α‐ and β‐D‐alloses was performed, including molecular dynamics (MD) simulations, high‐level geometry optimizations, and GIAO‐DFT NMR studies. Generally, a good correlation between calculated 1H and 13C NMR chemical shifts of the conformationally averaged α‐ and β‐D‐alloses against experiment was found. Based on the performed calculations, the optimal combination of functionals with basis sets for the geometry optimization (M06‐2X/aug‐pc‐2) and NMR calculations (BHandHLYP/aug‐pcSseg‐2) for carbohydrates was suggested. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Physical Organic Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
FullText Text:
  Availability: 0
Header DbId: egs
DbLabel: Engineering Source
An: 193057806
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Computational NMR of Carbohydrates. 2. Allopyranoses: Theoretical Conformational Analysis and NMR Calculations.
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Fedorov%2C+Sergei V%2E%22">Fedorov, Sergei V.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Semenov%2C+Valentin A%2E%22">Semenov, Valentin A.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Krivdin%2C+Leonid B%2E%22">Krivdin, Leonid B.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> krivdin55@gmail.com</i>
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="JN" term="%22Journal+of+Physical+Organic+Chemistry%22">Journal of Physical Organic Chemistry</searchLink>. May2026, Vol. 39 Issue 5, p1-13. 13p.
– Name: Subject
  Label: Subjects
  Group: Su
  Data: <searchLink fieldCode="DE" term="%22Carbohydrates%22">Carbohydrates</searchLink><br /><searchLink fieldCode="DE" term="%22Conformational+analysis%22">Conformational analysis</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+dynamics%22">Molecular dynamics</searchLink><br /><searchLink fieldCode="DE" term="%22Density+functional+theory%22">Density functional theory</searchLink><br /><searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance%22">Nuclear magnetic resonance</searchLink><br /><searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance+spectroscopy%22">Nuclear magnetic resonance spectroscopy</searchLink><br /><searchLink fieldCode="DE" term="%22Pyranoses%22">Pyranoses</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Allose, an aldohexose sugar, is a rare natural monosaccharide that occurs in nature in the form of a 6‐O‐cinnamyl glycoside in the leaves of the African shrub Protea rubropilosa. It differs from glucose in the orientation of the hydroxyl group at the C‐3 position, being thus the C‐3 substituted epimer of glucopyranose. In this paper, a detailed theoretical modeling of α‐ and β‐D‐alloses was performed, including molecular dynamics (MD) simulations, high‐level geometry optimizations, and GIAO‐DFT NMR studies. Generally, a good correlation between calculated 1H and 13C NMR chemical shifts of the conformationally averaged α‐ and β‐D‐alloses against experiment was found. Based on the performed calculations, the optimal combination of functionals with basis sets for the geometry optimization (M06‐2X/aug‐pc‐2) and NMR calculations (BHandHLYP/aug‐pcSseg‐2) for carbohydrates was suggested. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Physical Organic Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=193057806
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1002/poc.70079
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 13
        StartPage: 1
    Subjects:
      – SubjectFull: Carbohydrates
        Type: general
      – SubjectFull: Conformational analysis
        Type: general
      – SubjectFull: Molecular dynamics
        Type: general
      – SubjectFull: Density functional theory
        Type: general
      – SubjectFull: Nuclear magnetic resonance
        Type: general
      – SubjectFull: Nuclear magnetic resonance spectroscopy
        Type: general
      – SubjectFull: Pyranoses
        Type: general
    Titles:
      – TitleFull: Computational NMR of Carbohydrates. 2. Allopyranoses: Theoretical Conformational Analysis and NMR Calculations.
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Fedorov, Sergei V.
      – PersonEntity:
          Name:
            NameFull: Semenov, Valentin A.
      – PersonEntity:
          Name:
            NameFull: Krivdin, Leonid B.
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 01
              M: 05
              Text: May2026
              Type: published
              Y: 2026
          Identifiers:
            – Type: issn-print
              Value: 08943230
          Numbering:
            – Type: volume
              Value: 39
            – Type: issue
              Value: 5
          Titles:
            – TitleFull: Journal of Physical Organic Chemistry
              Type: main
ResultId 1