Work

A Convenient Route to Large-Scale Chemical Synthesis of p-Hydroxyphenylacetaldehyde Oxime and Its p-β- d -Glucopyranoside: Key Intermediates and Products in Plant Specialized Metabolism

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Oximes are unrecognized chameleons in general and specialized plant metabolism. E- and Z-p -hydroxyphenylacetaldehyde oxime are key intermediates in the biosynthesis of the cyanogenic glucoside dhurrin produced in sorghum. Nevertheless, none of the geometrical oxime isomers accumulate in the plant. Herein, we report a convenient route to the chemical synthesis of E- and Z-p -hydroxyphenylacetaldehyde oxime and its biologically produced p -β- d -glucopyranoside using p -hydroxyphenylacetic acid as a starting material. This starting material is also available in radiolabeled forms. All reaction steps proceeded with excellent yield under mild conditions, operational facility, and scalability.

Source: ACS Omega

DOI: 10.1021/acsomega.4c05014

Authors: Birger Lindberg Møller, Carl Erik Olsen, Yong Zhao, Mohammed Saddik Motawie

Institution: University of Copenhagen

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funders: Villum Fonden, Københavns Universitet, Carlsbergfondet