Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein. Academic Article

abstract

• The terpenoid gossypol, a secondary metabolite found in the cotton plant, is synthesized by a free radical dimerization of hemigossypol. Gossypol exists as an atropisomeric mixture because of restricted rotation around the central binaphthyl bond. The dimerization of hemigossypol is regiospecific in cotton. In the case of some moco cotton, the dimerization also exhibits a high level of stereoselectivity. The mechanism that controls this stereoselective dimerization is poorly understood. In this paper, we demonstrate that a dirigent protein controls this stereoselective dimerization process. A partially purified protein preparation from cotton flower petals, which by itself is unable to convert hemigossypol to gossypol, converts hemigossypol with a 30% atropisomeric excess into (+)-gossypol when combined with an exogenous laccase, which by itself produces racemic gossypol.

authors

• Magill, Clint

published proceedings

• Phytochemistry

author list (cited authors)

• Liu, J., Stipanovic, R. D., Bell, A. A., Puckhaber, L. S., & Magill, C. W.

citation count

• 68

complete list of authors

• Liu, Jinggao||Stipanovic, Robert D||Bell, Alois A||Puckhaber, Lorraine S||Magill, Clint W

publication date

• December 2008

publisher

• Elsevier  Publisher

published in

• Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology  Journal

keywords

• Gene Expression Regulation, Plant
• Gossypium
• Gossypol
• Molecular Structure
• Plant Proteins

PubMed Central ID

• 18639908

Digital Object Identifier (DOI)

• 10.1016/j.phytochem.2008.06.007

start page

• 3038

end page

• 3042

volume

• 69

issue

• 18

URL

• http://dx.doi.org/10.1016/j.phytochem.2008.06.007