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Comparison of acidity and metal ion affinity of D-Glucosamine and N-acetyl-D-glucosamine, a DFT study.
- Source :
-
Journal of Molecular Graphics & Modelling . Jul2020, Vol. 98, pN.PAG-N.PAG. 1p. - Publication Year :
- 2020
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Abstract
- The derivatives of glucose such as glucosamine (β-D-GlcN) and N-acetyl-D-β-glucosamine (GlcNAc) are significant in several biological systems. D-GlcN has been used widely to treat osteoarthritis in humans and animal models as well as GlcNAc has been proposed as a treatment for autoimmune diseases. The DFT/B3LYP/6–311++G (d,p) method as well as QTAIM and NBO analyses were used to the acidity values of D-GlcN and GlcNAc sugars and their complexes with alkali ions in the gas phase. The Li+, Na+ and K+ prefer bi-dentate chelate in these complexes. The computed results indicate that metal ion affinity (MIA) in GlcNAc is higher than that in D-GlcN. There are direct correlations between the MIA values of D-GlcN and GlcNAc sugars and the atomic numbers of Li, Na, and K. The calculated acidity values for GlcNAc at C 2 –NH and C 6 –HO 6 sites are 331 and 333 kcal mol−1, respectively. Whereas the calculated acidity values for D-GlcN at C 2 –NH and C 6 –HO 6 sites are 365 and 372 kcal mol−1, respectively. The AIM and NBO analyses indicate the presence of intramolecular H-bonds in GlcNAc sugar in both its neutral form and conjugate base; whereas D-GlcN indicates intramolecular H-bonds in only its conjugate base. Image 1 • Hydrogen bonding effect on Acidity of d -Glucosamine and N-Acetyl- d -Glucosamine. • Metal Ion Affinity of d -Glucosamine and N-Acetyl- d -Glucosamine. • D-Glucosamine and N-acetyl-D-glucosamine as ideal cation exchangers models. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 10933263
- Volume :
- 98
- Database :
- Academic Search Index
- Journal :
- Journal of Molecular Graphics & Modelling
- Publication Type :
- Academic Journal
- Accession number :
- 143310915
- Full Text :
- https://doi.org/10.1016/j.jmgm.2020.107612