Premium
The Preferred Conformations of Glycosylalditols
Author(s) -
Lichtenthaler Frieder W.,
Lindner Hans J.
Publication year - 1981
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198119811221
Subject(s) - zigzag , chemistry , bent molecular geometry , chain (unit) , ring (chemistry) , stereochemistry , crystallography , planar , anomer , section (typography) , geometry , physics , organic chemistry , mathematics , computer science , astronomy , computer graphics (images) , operating system
Crystal structure analysis shows 6‐ O ‐(α‐D‐glucopyranosyl)‐D‐glucitol (isomaltitol 1 ) to have a bent glucitol chain linked to glucose in normal 4 C 1 ‐chair form, the middle section forming a planar zigzag chain that extends into the pyranoid ring. Comparative assessment of the conformational features of 1 , its D‐mannitol analogue 2 , and of some (1 → 4)‐linked analogues allows — in combination with Jeffrey's alditol rules and the exo ‐anomeric effect principles — to predict with significant confidence the preferred conformations of glycosylalditols in general.