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Glycan Stability an...
Glycan Stability and Flexibility : Thermodynamic and Kinetic Characterization of Nonconventional Hydrogen Bonding in Lewis Antigens
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Kwon, Jeahoo (author)
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- Ruda, Alessandro, 1990- (author)
- Stockholms universitet,Institutionen för organisk kemi
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Azurmendi, Hugo F. (author)
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Zarb, Jasmin (author)
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Battistel, Marcos D. (author)
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Liao, Liang (author)
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Asnani, Ari (author)
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Auzanneau, France-Isabelle (author)
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- Widmalm, Göran (author)
- Stockholms universitet,Institutionen för organisk kemi
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Freedberg, Daron I. (author)
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(creator_code:org_t)
- 2023
- 2023
- English.
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In: Journal of the American Chemical Society. - 0002-7863 .- 1520-5126. ; 145:18, s. 10022-10034
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https://doi.org/10.1...
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https://urn.kb.se/re...
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Abstract
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- We provide evidence for CH-based nonconventional hydrogen bonds (H-bonds) for 10 Lewis antigens and two of their rhamnose analogues. We also characterize the thermodynamics and kinetics of the H-bonds in these molecules and present a plausible explanation for the presence of nonconventional H-bonds in Lewis antigens. Using an alternative method to simultaneously fit a series of temperature-dependent fast exchange nuclear magnetic resonance (NMR) spectra, we determined that the H-bonded conformation is favored by ∼1 kcal/mol over the non-H-bonded conformation. Additionally, a comparison of temperature-dependent 13C linewidths in various Lewis antigens and the two rhamnose analogues reveals H-bonds between the carbonyl oxygen of the N-acetyl group of N-acetylglucosamine and the OH2 group of galactose/fucose. The data presented herein provide insight into the contribution of nonconventional H-bonding to molecular structure and could therefore be used for the rational design of therapeutics.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Kwon, Jeahoo
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Ruda, Alessandro ...
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Azurmendi, Hugo ...
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Zarb, Jasmin
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Battistel, Marco ...
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Liao, Liang
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show more...
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Asnani, Ari
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Auzanneau, Franc ...
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Widmalm, Göran
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Freedberg, Daron ...
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show less...
- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
- Articles in the publication
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Journal of the A ...
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Stockholm University