Optimization of synthesis of carbohydrates and 1-phenyl-3-methyl-5-pyrazolone (PMP) by response surface methodology (RSM) for improved carbohydrate detection

Weizheng Wang; Feng Chen; Fuping Zheng; Brook T Russell

doi:10.1016/j.foodchem.2019.125686

Optimization of synthesis of carbohydrates and 1-phenyl-3-methyl-5-pyrazolone (PMP) by response surface methodology (RSM) for improved carbohydrate detection

Food Chem. 2020 Mar 30:309:125686. doi: 10.1016/j.foodchem.2019.125686. Epub 2019 Oct 19.

Authors

Weizheng Wang¹, Feng Chen², Fuping Zheng³, Brook T Russell⁴

Affiliations

¹ Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China; Department of Food, Nutrition and Packaging Sciences, Clemson University, Clemson, SC 29634, USA; Department of Biological System Engineering, University of Wisconsin-Madison, WI 53706, USA.
² Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China; Department of Food, Nutrition and Packaging Sciences, Clemson University, Clemson, SC 29634, USA. Electronic address: fchen@clemson.edu.
³ Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China; Department of Food, Nutrition and Packaging Sciences, Clemson University, Clemson, SC 29634, USA.
⁴ Department of Mathematical Sciences, Clemson University, Clemson, SC 29634, USA.

PMID: 31670130
DOI: 10.1016/j.foodchem.2019.125686

Abstract

Reducing sugars can react with 1-phenyl-3-methyl-5-pyrazolone (PMP) to form sugar-PMP derivatives, which can be detected by HPLC-UV or HPLC-DAD due to their high UV absorbance at 248 nm. Six different sugars were synthesized with PMP with aid of response surface methodology (RSM), by which the parameters of the synthesis were designed within temperature ranged between 60 °C and 90 °C, and time from 60 to 180 min, respectively. Consequently, optimal conditions of the glucose (Glu)-, glucosamine (GluN)-, galactose (Gal)-, glucuronic acid (GluA), galacturonic acid (GalA) and glucose-6-phosphate (G6P-PMP) reactions were determined at 71 °C for 129 min, 73 °C for 96 min, 70 °C for 117 min, 75 °C for 151 min, 76 °C for 144 min, and 70 °C for 154 min, respectively. Experiments demonstrated that unique functional groups and delicate differences of carbohydrates' inner pH environment could significantly influence the sugar-PMP reactions. However, sugar stereoisomers did not have remarkable impacts on the reactions.

Keywords: HPLC; PMP; RSM; Reducing sugar.

MeSH terms

Carbohydrates / analysis*
Carbohydrates / chemistry*
Chromatography, High Pressure Liquid
Edaravone / chemistry*
Galactose / analysis
Galactose / chemistry
Glucosamine / analysis
Glucosamine / chemistry
Glucose / analysis
Glucose / chemistry
Glucose-6-Phosphate / analysis
Glucose-6-Phosphate / chemistry
Glucuronic Acid / analysis
Glucuronic Acid / chemistry
Hexuronic Acids / analysis
Hexuronic Acids / chemistry
Stereoisomerism

Substances

Carbohydrates
Hexuronic Acids
galacturonic acid
Glucose-6-Phosphate
Glucuronic Acid
Glucose
Glucosamine
Edaravone
Galactose