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

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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]
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Database: Engineering Source
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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]
ISSN:08943230
DOI:10.1002/poc.70079