Methyl 4-O-beta-D-galactopyranosyl alpha-D-mannopyranoside methanol 0.375-solvate.
Methyl beta-D-galactopyranosyl-(1-->4)-alpha-D-mannopyranoside methanol 0.375-solvate, C(13)H(24)O(11).0.375CH(3)OH, (I), was crystallized from a methanol-ethanol solvent system in a glycosidic linkage conformation, with varphi' (O5(Gal)-C1(Gal)-O1(Gal)-C4(Man)) = -68.2 (3) degrees and psi' (C1(Gal)-O1(Gal)-C4(Man)-C5(Man)) = -123.9 (2) degrees , where the ring is defined by atoms O5/C1-C5 (monosaccharide numbering); C1 denotes the anomeric C atom and C6 the exocyclic hydroxymethyl C atom in the betaGalp and alphaManp residues, respectively. The linkage conformation in (I) differs from that in crystalline methyl alpha-lactoside [methyl beta-D-galactopyranosyl-(1-->4)-alpha-D-glucopyranoside], (II) [Pan, Noll & Serianni (2005). Acta Cryst. C61, o674-o677], where varphi' is -93.6 degrees and psi' is -144.8 degrees . An intermolecular hydrogen bond exists between O3(Man) and O5(Gal) in (I), similar to that between O3(Glc) and O5(Gal) in (II). The structures of (I) and (II) are also compared with those of their constituent residues, viz. methyl alpha-D-mannopyranoside, methyl alpha-D-glucopyranoside and methyl beta-D-galactopyranoside, revealing significant differences in the Cremer-Pople puckering parameters, exocyclic hydroxymethyl group conformations and intermolecular hydrogen-bonding patterns.
Hu
Xiaosong
X
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556-5670, USA.
Pan
Qingfeng
Q
Noll
Bruce C
BC
Oliver
Allen G
AG
Serianni
Anthony S
AS
D018360:Crystallography, X-Ray; D000432:Methanol; D008759:Methylglycosides / Q000737:chemistry*; D008766:Methylmannosides / Q000737:chemistry*; D008958:Models, Molecular
D008759:Methylglycosides; D008766:Methylmannosides; C008466:methylmannoside; C034207:methyl lactoside; D000432:Methanol