Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

Isopropyl 3-deoxy-α-D-ribo-hexopyranoside (isopropyl 3-deoxy-α-D-glucopyranoside): evaluating trends in structural parameters

Journal Article · · Acta Crystallographica. Section C, Structural Chemistry (Online)
 [1];  [2];  [2];  [3];  [2]
  1. Univ. of Notre Dame, IN (United States). Dept. of Chemistry and Biochemistry; Univ. of Notre Dame, IN (United States)
  2. Univ. of Notre Dame, IN (United States). Dept. of Chemistry and Biochemistry
  3. Univ. of Notre Dame, IN (United States). Radiation Lab.
+ Show Author Affiliations

Isopropyl 3-de­oxy-α-D-ribo-hexo­pyran­oside (isopropyl 3-de­oxy-α-D-gluco­py­ran­oside), C9H18O5, (I), crystallizes from a methanol–ethyl acetate solvent mixture at room temperature in a 4C1 chair con­form­ation that is slightly dis­torted towards the C5SC1 twist-boat form. A com­parison of the structural parameters in (I), methyl α-D-gluco­pyran­oside, (II), α-D-gluco­pyranosyl-(1→4)-D-glucitol (maltitol), (III), and 3-de­oxy-α-D-ribo-hexo­pyran­ose (3-de­oxy-α-D-gluco­pyran­ose), (IV), shows that most endocyclic and exocyclic bond lengths, valence bond angles and torsion angles in the aldohexo­pyranosyl rings are more affected by anomeric configuration, aglycone structure and/or the con­form­ation of exocyclic substituents, such as hy­droxy­methyl groups, than by mono­deoxy­genation at C3. The structural effects observed in the crystal structures of (I)–(IV) were confirmed though density functional theory (DFT) calculations in com­puted structures (I)c–(IV)c. Exocyclic hy­droxy­methyl groups adopt the gauche–gauche (gg) con­form­ation (H5 anti to O6) in (I) and (III), and the gauche–trans (gt) con­form­ation (C4 anti to O6) in (II) and (IV). The O-glycoside linkage con­form­ations in (I) and (III) resemble those observed in disaccharides containing β-(1→4) linkages.

Research Organization:
University of Notre Dame, IN (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
FC02-04ER15533
OSTI ID:
1849017
Journal Information:
Acta Crystallographica. Section C, Structural Chemistry (Online), Journal Name: Acta Crystallographica. Section C, Structural Chemistry (Online) Journal Issue: 8 Vol. 77; ISSN 2053-2296; ISSN ACSCGG
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
English

References (32)

Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis: Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis journal February 2019
Synthesis of stereospecifically labeled 3,6-dideoxyhexoses journal June 1990
A redetermination of the crystal and molecular structure of maltitol (4-O-α-d-glucopyranosyl-d-glucitol) journal December 1999
Use of Circular Statistics To Model αMan-(1→2)-αMan and αMan-(1→3)-α/βMan O -Glycosidic Linkage Conformation in 13 C-Labeled Disaccharides and High-Mannose Oligosaccharides journal December 2018
Synthesis and O -Glycosidic Linkage Conformational Analysis of 13 C-Labeled Oligosaccharide Fragments of an Antifreeze Glycolipid journal January 2019
O -Acetyl Side-Chains in Monosaccharides: Redundant NMR Spin-Couplings and Statistical Models for Acetate Ester Conformational Analysis journal December 2016
Conformational Populations of β-(1→4) O -Glycosidic Linkages Using Redundant NMR J -Couplings and Circular Statistics journal March 2017
Encoding and decoding hydrogen-bond patterns of organic compounds journal April 1990
Observation of hydroxyl protons of sucrose in aqueous solution: no evidence for persistent intramolecular hydrogen bonds journal June 1992
Torsional effects on the one-bond 13C-13C spin coupling constant in ethylene glycol: insights into the behavior of 1JCC in carbohydrates journal November 1993
General definition of ring puckering coordinates journal March 1975
Correlated C−C and C−O Bond Conformations in Saccharide Hydroxymethyl Groups:  Parametrization and Application of Redundant 1 H− 1 H, 13 C− 1 H, and 13 C− 13 C NMR J -Couplings journal December 2004
Effect of Solvation on the Rotation of Hydroxymethyl Groups in Carbohydrates journal October 1998
DFT and NMR Studies of 2 J COH , 3 J HCOH , and 3 J CCOH Spin-Couplings in Saccharides:  C−O Torsional Bias and H-Bonding in Aqueous Solution journal September 2007
Fast Evaluation of Geometries and Properties of Excited Molecules in Solution:  A Tamm-Dancoff Model with Application to 4-Dimethylaminobenzonitrile journal June 2000
NMR spectroscopy of hydroxyl protons in supercooled carbohydrates journal April 1994
1021. The separation of isomeric glycosides on basic ion-exchange resins journal January 1963
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions journal January 1980
Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18 journal May 1980
Density‐functional thermochemistry. III. The role of exact exchange journal April 1993
A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics journal August 1997
A Conformational Study of Hydroxymethyl Groups in Carbohydrates Investigated by 1 H NMR Spectroscopy journal June 1994
3-Deoxy-β- D - ribo -hexopyranose (3-deoxy-β- D -glucopyranose) journal September 2007
Methyl β-lactoside (methyl 4- O -β- D -galactopyranosyl-β- D -glucopyranoside) methanol solvate journal October 1999
A short history of SHELX journal December 2007
A neutron diffraction study of the hydrogen bonding in the crystal structures of methyl α-D-mannopyranoside and methyl α-D-glucopyranoside journal March 1977
Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination journal January 2015
Mercury 4.0 : from visualization to analysis, design and prediction journal February 2020
Use of intensity quotients and differences in absolute structure refinement journal May 2013
Crystal structure refinement with SHELXL journal January 2015
O -Benzoyl side-chain conformations in 2,3,4,6-tetra- O -benzoyl-β- D -galactopyranosyl-(1→4)-1,2,6-tri- O -benzoyl-β- D -glucopyranose (ethyl acetate solvate) and 1,2,4,6-tetra- O -benzoyl-β- D -glucopyranose (acetone solvate) journal January 2019
SHELXT – Integrated space-group and crystal-structure determination journal January 2015

Similar Records

Reactions of the N-isopropyl-α-chloroketimines with P{sup IV} dithioacids
Journal Article · Fri Dec 14 23:00:00 EST 2018 · Russian Chemical Bulletin · OSTI ID:22943332
Comparison of the structures and elicitor activities of a synthetic and a mycelial-wall-derived hexa(. beta. -D-glucopyranosyl)-D-glucitol
Journal Article · Tue Sep 25 00:00:00 EDT 1984 · J. Biol. Chem.; (United States) · OSTI ID:5273051
The Structure of the L-myo-inositol-1-phosphate Synthase-NAD[superscript +]-2-deoxy-D-glucitol 6-(E)-Vinylhomophosphonate Complex Demands a Revision of the Enzyme Mechanism
Journal Article · Mon Nov 15 23:00:00 EST 2010 · J. Biol. Chem. · OSTI ID:1008749

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
DFT
chemical synthesis
chemistry
crystal structure
crystallography
isopropyl 3-de­oxy-α-D-gluco­pyran­oside
isopropyl 3-de­oxy-α-D-ribo-hexo­pyran­oside