β-d-Galacto-pyranosyl-(1→4)-2-amino-2-de-oxy-α-d-gluco-pyran-ose hydro-chloride monohydrate (lactosamine)

Valeri V Mossine; Steven P Kelley; Thomas P Mawhinney

doi:10.1107/S241431462200061X

β-d-Galacto-pyranosyl-(1→4)-2-amino-2-de-oxy-α-d-gluco-pyran-ose hydro-chloride monohydrate (lactosamine)

IUCrdata. 2022 Jan 28;7(Pt 1):x220061. doi: 10.1107/S241431462200061X. eCollection 2022 Jan.

Authors

Valeri V Mossine¹, Steven P Kelley², Thomas P Mawhinney¹

Affiliations

¹ Department of Biochemistry, University of Missouri, Columbia, MO 65211, USA.
² Department of Chemistry, University of Missouri, Columbia, MO 65211, USA.

Abstract

The title compound, C₁₂H₂₄NO₁₀ ⁺·Cl^-·H₂O, (I), crystallizes in the monoclinic space group P2₁ and exists as a monohydrate of a monosubstituted ammonium chloride salt, with the reducing carbohydrate portion existing exclusively as the α-pyran-ose tautomer. The glycosidic bond geometry in (I) is stabilized by an intra-molecular hydrogen bond and is close to that found in crystalline α-lactose. All heteroatoms except gluco-pyran-ose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of (I).

Keywords: Heyns rearrangement; crystal structure; glycosidic bond geometry; hydrogen bonding.

Grants and funding

Funding for this research was provided by: University of Missouri, Agriculture Experiment Station Chemical Laboratories; National Institute of Food and Agriculture (grant No. Hatch 1023929).