Confirmation of the absolute configuration of Stachybotrin C using single-crystal X-ray diffraction analysis of its 4-bromobenzyl ether derivative

Yu Kuroda; Keiko Hasegawa; Keiichi Noguchi; Kazuhiro Chiba; Keiji Hasumi; Yoshikazu Kitano

doi:10.1038/s41429-018-0042-2

Confirmation of the absolute configuration of Stachybotrin C using single-crystal X-ray diffraction analysis of its 4-bromobenzyl ether derivative

J Antibiot (Tokyo). 2018 Jun;71(6):584-591. doi: 10.1038/s41429-018-0042-2. Epub 2018 Mar 19.

Authors

Yu Kuroda¹, Keiko Hasegawa¹, Keiichi Noguchi², Kazuhiro Chiba¹, Keiji Hasumi¹, Yoshikazu Kitano³

Affiliations

¹ Department of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan.
² Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
³ Department of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu-shi, Tokyo, 183-8509, Japan. kitayo@cc.tuat.ac.jp.

PMID: 29555967
DOI: 10.1038/s41429-018-0042-2

Abstract

The absolute configuration of Stachybotrin C was confirmed in this study. After synthesizing the dimethyl ethers of Stachybotrin C, the C-8 epimer was analyzed by 1D NOESY. However, the stereochemistry determination was difficult through the NOE correlations. Instead, the di(4-bromobenzyl) ether of Stachybotrin C was derived and used for X-ray diffraction analysis, because its single crystal was easier to obtain than that of the original Stachybotrin C. The stereochemistry of Stachybotrin C was determined to be (8S, 9R). This derivatization approach may also be used to prepare single crystals of the analogues.

MeSH terms

Benzopyrans / chemistry*
Crystallization
Indoles / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Molecular Structure
Nerve Growth Factors / chemistry*
Stereoisomerism
X-Ray Diffraction

Substances

Benzopyrans
Indoles
Nerve Growth Factors
stachybotrin C