NMR and X-ray studies of isomeric 22,23-dihydroxy stigmastanes

A comparative conformational study of steroidal side chain of (22 R,23 R)- and (22 S,23 S)-dihydroxy stigmastane derivatives was performed using single crystal X-ray diffraction and NMR spectroscopy. The preferred conformation in solution was shown to be close to that in the crystal. (22 R,23 R)-Iso...

Full description

Saved in:
Bibliographic Details
Published in:Journal of molecular structure 2010-06, Vol.975 (1), p.242-246
Main Authors: Khripach, Vladimir A., Zhabinskii, Vladimir N., Ivanova, Galina V., Fando, Galina P., Tsavlovskii, Dmitrii V., Khripach, Natalya B., Lyakhov, Alexander S., Misharin, Alexander Yu
Format: Article
Language:English
Subjects:
Brassinosteroids
Chains
Conformation
Derivatives
Diffraction
Hormones
Hydroxyl groups
Molecular conformation
Molecular structure
NMR spectroscopy
X-ray crystallography
X-rays
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A comparative conformational study of steroidal side chain of (22 R,23 R)- and (22 S,23 S)-dihydroxy stigmastane derivatives was performed using single crystal X-ray diffraction and NMR spectroscopy. The preferred conformation in solution was shown to be close to that in the crystal. (22 R,23 R)-Isomers typical for natural plant steroid hormones brassinosteroids adopt a conformation in which both hydroxyl groups are pointed toward unhindered α-side of the steroidal plane and can thus participate in biochemical processes. Unnatural (22 S,23 S)-counterparts exhibit a conformation with the two hydroxyl groups oriented in the opposite direction and sterically hindered by 21-methyl group and terminal side chain fragment.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2010.04.030