Crystal packing in three related disaccharides: precursors to heparan sulfate oligosaccharides

Acta Crystallographica Section E: Crystallographic Communications

Gainsford, G.J.¹  rer, R.²  Tyler, P.C.²  Schwö² 

[1] CallaghanInnovation, PO Box 31-310, Lower Hutt 5040, New Zealand;Ferrier Research Institute, Victoria University of Wellington, PO Box 33 436, Petone, Lower Hutt 5046, New Zealand

关键词: CRYSTAL STRUCTURE;    DISACCHARIDE;    ALZHEIMER'S;    SYNTHESIS;    HYDROGEN BONDING;    C-H...[PI] CONTACTS;   

DOI  :  10.1107/S2056989015008518

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The three title compounds form part of a set of important precursor dissacharides which lead to novel therapeutics, in particular for Alzheimer's disease. All three crystallize as poorly diffracting crystals with one independent mol­ecule in the asymmetric unit. Two of them are isostructural: 4-meth­oxy­phenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-de­oxy-4-O-(9-fluor­en­yl­methyl­oxycarbon­yl)-α-d-gluco­pyranos­yl]-2-O-benzoyl-3-O-benzyl-6-O-chloro­acetyl-α-l-ido­pyran­oside, C59H56ClN3O16, (I), the ido-relative of a reported gluco-disaccharide [Gainsford et al., 2013). Acta Cryst. C69, 679–682] and 4-meth­oxy­phenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-de­oxy-4-O-(9-fluorenyl­methyl­oxycarbon­yl)-α-d-gluco­pyranos­yl]-2-O-benzoyl-3-O-benzyl-6-O-meth­oxy­acetyl-α-l-ido­pyran­oside, C60H59N3O17, (II). Both exhibit similar conformational disorder of pendant groups. The third compound 4-meth­oxy­phenyl 4-O-[6-O-acetyl-2-azido-3,4-di-O-benzyl-2-de­oxy-α-d-gluco­pyranos­yl]-2-O-benzoyl-3-O-benzyl-6-O-meth­oxy­oacetyl-β-d-gluco­pyran­oside, C52H55N3O15, (III), illustrates that a slightly larger set of weak inter­molecular inter­actions can result in a less disordered mol­ecular arrangement. The mol­ecules are bound by weak C—H⋯O(ether) hydrogen bonds in (I) and (II), augmented by C—H⋯π inter­actions in (III). The absolute configurations were determined, although at varying levels of significance from the limited observed data.

【 授权许可】

CC BY