Skip to Main Content
U.S. Forest Service
Caring for the land and serving people

United States Department of Agriculture

Home > Search > Publication Information

  1. Crystal structure, conformational analysis, and molecular dynamics of tetra-0-methyl-(+)-catechin

    Share via EmailShare on FacebookShare on LinkedInShare on Twitter
    Dislike this pubLike this pub
    Author(s): Frank R. Fronczek; Richard W. Hemingway; G. Wayne McGraw; Jan P. Steynberg; Carin A. Helfer; Wayne L. Mattice
    Date: 1993
    Source: Biopolymers 33(275-282
    Publication Series: Miscellaneous Publication
    PDF: View PDF  (1.8 MB)

    Description

    The structure of tetra-O-methyl-(+)-catechin has been determined in the crystalline state. Two independent molecules, denoted structure A and structure B, exist in the unit cell. Crystals are triclinic, space group P1, a=4.8125(2) Ǻ, b=12.9148(8) Ǻ, c=13.8862(11) Ǻ, α=86.962(6)°, β=89.120(5)°, γ=88.044(5)°, Ζ=2, De=1.336 g cm-3, R=0.033 for 6830 observations. The heterocyclic rings of the crystal structures are compared to previous results for 8-bromotetra-O-methyl-(+)-catechin, penta-O-acetyl-(+)-catechin, and (-)-epicatechin. One of the two molecules has a heterocyclic ring conformation similar to that observed previously for (-)-epicatechin, and the other has a heterocyclic ring conformation similar to one predicted earlier in a theoretical analysis of dimera of (+)-catechin and (-)-epicatechin. Both structure A and structure B in the crystal have heterocyclic ring conformations that place the dimethoxyphenyl substituent at C(2) in the equatorial position. However. this heterocyclic ring conformation does not explain the proton nmr coupling constant measured in solution. Molecular dynamics simulations show an equatorial- axial interconversion of the heterocyclic ring, which can explain the nmr results.

    Publication Notes

    • You may send email to pubrequest@fs.fed.us to request a hard copy of this publication.
    • (Please specify exactly which publication you are requesting and your mailing address.)
    • We recommend that you also print this page and attach it to the printout of the article, to retain the full citation information.
    • This article was written and prepared by U.S. Government employees on official time, and is therefore in the public domain.

    Citation

    Fronczek, Frank R.; Hemingway, Richard W.; McGraw, G. Wayne; Steynberg, Jan P.; Helfer, Carin A.; Mattice, Wayne L. 1993. Crystal structure, conformational analysis, and molecular dynamics of tetra-0-methyl-(+)-catechin. Biopolymers 33(275-282

    Related Search

    XML: View XML
Show More
Show Fewer
Jump to Top of Page
https://www.fs.usda.gov/treesearch/pubs/8001