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Structures of furanosides: geometrical analysis of low- temperature X-ray and neutron crystal structures of five crystalline methyl pentofuranosides

  1. Author:
    Evdokimov, A.
    Gilboa, A. J.
    Koetzle, T. F.
    Klooster, W. T.
    Schultz, A. J.
    Mason, S. A.
    Albinati, A.
    Frolow, F.

  2. Author Address

    NCI, Prot Engn Sect, Program Struct Biol, Frederick Canc Res & Dev Ctr, POB B, Frederick, MD 21702 USA. NCI, Prot Engn Sect, Program Struct Biol, Frederick Canc Res & Dev Ctr, Frederick, MD 21702 USA. Weizmann Inst Sci, Dept Biol Struct, IL-76100 Rehovot, Israel. Brookhaven Natl Lab, Dept Chem, Upton, NY 11973 USA. Argonne Natl Lab, Div Intense Pulsed Neutron Source, Argonne, IL 60439 USA. Inst Max Von Laue Paul Langevin, F-38042 Grenoble 9, France. Univ Milan, Ist Chim Farmaceut, I-20131 Milan, Italy. Tel Aviv Univ, George S Wise Fac Life Sci, IL-69978 Tel Aviv, Israel. Evdokimov A NCI, Prot Engn Sect, Program Struct Biol, Frederick Canc Res & Dev Ctr, POB B, Frederick, MD 21702 USA.
    1. Year: 2001
  2. Journal: Acta Crystallographica Section B-Structural Science
    1. 57
    2. Pt. 2
    3. Pages: 213-220
  4. Type of Article: Article
  1. Abstract:

    Crystal structures of all five crystalline methyl D- pentofuranosides, methyl alpha -D-arabinofuranoside (1), methyl beta -D-arabinofuranoside (2), methyl alpha -D-lyxofuranoside (3), methyl beta -D-ribofuranoside (4) and methyl alpha -D- xylofuranoside (5) have been determined by means of cryogenic X-ray and neutron crystallography. The neutron diffraction experiments provide accurate. unbiased H-atom positions which are especially important because of the critical role of hydrogen bonding in these systems. This paper summarizes the geometrical and conformational parameters of the structures of all five crystalline methyl pentofuranosides, several of them reported here for the first time. The methyl pentofuranoside structures are compared with the structures of the five crystalline methyl hexopyranosides for which accurate X-ray and neutron structures have been determined. Unlike the methyl hexopyranosides, which crystallize exclusively in the C-1 chair conformation, the five crystalline methyl pentofuranosides represent a very wide range of ring conformations.

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