NMR and MS Analysis of Decomposition Compounds Produced from N-Acetyl-L-glutamine at Low pH
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文摘
N-Acetyl-<FONT SIZE="-1">L-glutamine decomposition products glutamine, glutamic acid, pyroglutamic acid, N-acetylglutamic acid, and a novel compound, N-(2,6-dioxo-3-piperidinyl) acetamide, have beenidentified by NMR and MS techniques. N-Acetylglutamine, a modified amino acid, offers greaterchemical stability than glutamine in conditions that are experienced during typical sterilizationand shelf storage of liquid nutritionals. However, to support safety and stability studies, potentialdecomposition products of N-acetyl-L-glutamine needed to be identified. Therefore, atypically harshconditions were used; an unbuffered (pH <3) 1 mg/mL water solution of N-acetyl-L-glutamine washeated to 100 f">C for 3 h. One-dimensional proton and proton-decoupled carbon-13 NMR andelectrospray LC-MS/MS techniques were employed to identify the molecular structures of thegenerated N-acetyl-L-glutamine decomposition products. Additionally, DEPT and two-dimensionalNMR techniques TOCSY, GMQCOSY, GHSQC, and GHMBC were employed to derive the finalstructure of the acetamide.Keywords: Functional foods; NMR; LC-MS; HPLC; glutamine; N-acetylglutamine; decompositionproducts; stability

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