Determination of process-related impurities in N-acetylglucosamine prepared by chemical and enzymatic methods: structural elucidation and quantification

Yi Soo Kim, Sung Joong Lee, Jin Young Choi, Yun Hi Kim, Kebede Taye Desta, Zhe Piao, Su Lim Choi, Sang Jip Nam, Kyung Yun Kang, A. M. Abd El-Aty, Yong Chul Shin, Sung Chul Shin

Research output: Contribution to journalArticlepeer-review

Abstract

β-N-acetylglucosamine (β-AG) is a monosaccharide distributed widely in living organisms with various pivotal roles. The presence of particulates and impurities can affect the safety and efficacy of a product for its intended duration of use. Thus, the current study was carried out to identify and quantify the potentially-harmful process related impurities; namely α-N,6-diacetylglucosamine (α-DAG) and α-N-acetylglucosamine (α-AG), derived from the chemical and enzymatic synthesis of β-AG. The impurities were characterized using a high resolution mass spectrometry, a nuclear magnetic resonance spectroscopy, and liquid chromatography-tandem mass spectrometry (LC/MS/MS). The developed method showed a good linearity (R2 ≥ 0.998), satisfactory precision (≤6.1 % relative standard deviation), intra- and inter-day accuracy (88.20–97.50 %), extraction recovery (89.30–110.50 %), matrix effect (89.70–105.20 %), and stability (92.70–101.60 %). The method was successfully applied to determine the level of α-DAG that was 3.04 and 0.07 % of the total β-AG, following chemical and enzymatic methods, respectively. It can be concluded that the enzymatic rather than the chemical method is more efficient for the synthesis of β-AG. Characterization of impurities heeds the signal for acquiring and evaluating data that establishes biological safety.

Original languageEnglish
Pages (from-to)937-945
Number of pages9
JournalArchives of Pharmacal Research
Volume39
Issue number7
DOIs
StatePublished - 1 Jul 2016

Keywords

  • Chitin
  • Nuclear magnetic resonance
  • Process-related impurity
  • Tandem mass spectrometry
  • β-N-acetylglucosamine

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