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Glutamine and Asparagine in Nutritional Products

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Abstract

Glutamine and asparagine in enteral therapeutic nutritional products, and in the milk, casein, soy, and whey protein ingredients with which they were formulated, have been estimated by an indirect approach: from published amino acid sequence and individual protein distribution data. A second set of estimates, based on experimental GLX and ASX determinations, differed by ≤ 10% from the sequence-based estimates. Further corroboration was obtained by determinations of amide nitrogen, which also differed by ≤ 10% from the sum of the estimated glutamine + asparagine. Determinations of GLX, ASX, and amide nitrogen were also used to estimate glutamine and asparagine in wheat protein ingredients and in wheat protein–fortified nutritional products. The resistance of protein-bound glutamine and asparagine to deamidation during nutritional product processing was verified. Free ammonia in protein hydrolysates was correlated with degree of hydrolysis, suggesting that glutamine content decreases as the degree of hydrolysis increases. The study indicates that, pending comparison and verification by direct enzymatic hydrolysis methods of glutamine and asparagine determination, the concentrations in common protein ingredients and in many commercial nutritional products may be reliably estimated from published data.

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References

  • Arntfield SD, Murray ED (1981) Determination of amide nitrogen in plant proteins using an ammonia electrode. Can Inst Food Sci Technol J 14:227–229

    Article  CAS  Google Scholar 

  • Baldwin MA, Falick AM, Gibson BW, Prusiner SB, Stahl N, Burlingame AL (1990) Tandem mass spectrometry of peptides with N-terminal glutamine. Studies on a prion protein peptide. J Am Soc Mass Spectrom 1:258–264

    Article  CAS  Google Scholar 

  • Baxter JH, Phillips RR, Dowlati L, Johns PW (2004) Glutamine in commercial liquid nutritional products. J Agric Food Sci 52:4963–4968

    Article  CAS  Google Scholar 

  • Chin CCQ, Wold F (1974) The preparation of matrix-bound proteases and their use in the hydrolysis of proteins. Anal Biochem 61:379–391

    Article  CAS  Google Scholar 

  • Church FC, Swaisgood HE, Catignani GL (1984) Compositional analysis of proteins following hydrolysis by immobilized proteases. J Appl Biochem 6:205–211

    CAS  PubMed  Google Scholar 

  • Creighton TE (1993) Proteins. Structures and molecular properties, 2nd edn. W.H. Freeman and Company, New York, p 9

    Google Scholar 

  • Ewaschuk JB, Murdoch GK, Johnson IR, Madsen KL, Field CJ (2011) Glutamine supplementation improves intestinal barrier function in a weaned piglet model of Escherichia coli infection. Br J Nutr 106:870–877

    Article  CAS  Google Scholar 

  • Fouques D, Landry J (1991) Study of the conversion of asparagine and glutamine of proteins into diaminopropionic acid and diaminobutyric acid using [bis (trifluoroacetoxy)iodo] benzene prior to amino acid derivatization. Analyst 116:529–531

    Article  CAS  Google Scholar 

  • Giesler L, Linke D, Rabe S, Appel D, Gunter Berger R (2013) Hydrolysis of wheat gluten by combining peptidases of Flammulina velutipes and electrodialysis. J Agric Food Chem 61:8641–8649

    Article  CAS  Google Scholar 

  • Harris RC, Hoffman JR, Allsopp A, Routledge NBH (2012) L-glutamine absorption is enhanced after ingestion of L-alanylglutamine compared with the free amino acid or wheat protein. Nutr Res 32(4):272–277

    Article  CAS  Google Scholar 

  • Haynes TE, Li P, Li X, Shimotori K, Sato H, Flynn NE, Wang J, Knabe DA, Wu G (2009) L-Glutamine or L-alanyl-L-glutamine prevents oxidant- or endotoxin-induced death of neonatal enterocytes. Amino Acids 37:131–142

    Article  CAS  Google Scholar 

  • Hertzler SR, Lieblein-Boff J, Weiler M, Allgeier C (2020) Plant proteins: assessing their nutritional quality and effects on health and physical function. Nutrients 12:3704

    Article  CAS  Google Scholar 

  • Hill RL, Schmidt WR (1962) The complete enzymic hydrolysis of proteins. J Biol Chem 237(2):389–397

    Article  CAS  Google Scholar 

  • Holt LA, Milligan B, Roxburgh CM (1971) Aspartic acid, asparagine, glutamic acid, and glutamine contents of wool and two derived protein fractions. Aust J Biol Sci 24:509–514

    Article  CAS  Google Scholar 

  • Hou Y, He W, Hu S, Wu G (2019) Composition of polyamines and amino acids in plant-source foods for human consumption. Amino Acids 51:1153–1165

    Article  CAS  Google Scholar 

  • Inglis AS, Roxburgh CM, Takayanagi H (1974) Analysis for amide nitrogen in proteins. Anal Biochem 61:25–31

    Article  CAS  Google Scholar 

  • Kempkes LJM, Martens J, Grzetic J, Berden G, Oomens J (2016) Deamidation reactions of asparagine- and glutamine-containing peptides investigated by ion spectroscopy. J Am Soc Mass Spectrom 27:1855–1869

    Article  CAS  Google Scholar 

  • Kuhn KS, Stehle P, Furst P (1996a) Quantitative analysis of glutamine in peptides and proteins. J Agric Food Chem 44:1808–1811

    Article  CAS  Google Scholar 

  • Kuhn KS, Stehle P, Furst P (1996b) Glutamine content of protein and peptide-based enteral products. J Parenter Enter Nutr 20:292–295

    Article  CAS  Google Scholar 

  • Lenders CM, Liu S, Wilmore DW, Sampson L, Dougherty LW, Spiegelman D, Willett WC (2009) Evaluation of a novel food composition database that includes glutamine and other amino acids derived from gene sequencing data. Eur J Clin Nutr 63:1433–1439

    Article  CAS  Google Scholar 

  • Li P, Wu G (2020) Composition of amino acids and related nitrogenous nutrients in feedstuff for animal diets. Amino Acids 52:523–542

    Article  CAS  Google Scholar 

  • Li X, Rezaei R, Li P, Wu G (2011) Composition of amino acids in feed ingredients for animal diets. Amino Acids 40:1159–1168

    Article  CAS  Google Scholar 

  • Moller AB, Andrews AT, Cheeseman GC (1977) Chemical changes in ultraheat-treated milk during storage. J Dairy Res 44:259–266

    Article  Google Scholar 

  • Newburg DS, Frankel DL, Fillios LC (1975) An asparagine requirement in young rats fed the dietary combination of aspartic acid, glutamine and glutamic acid. J Nutr 105:356–363

    Article  CAS  Google Scholar 

  • Shih FF (1985) Analysis of glutamine, glutamic acid, and pyroglutamic acid in protein hydrolysates by high-performance liquid chromatography. J Chromatogr 322:248–256

    Article  CAS  Google Scholar 

  • Shih FF (1990) Deamidation during treatment of soy protein with protease. J Agric Food Chem 55(1):127–132

    CAS  Google Scholar 

  • Soby LM, Johnson P (1981) Determination of asparagine and glutamine in polypeptides using bis(I,I-trifluoroacetoxy)-iodobenzene. Anal Biochem 113:149–153

    Article  CAS  Google Scholar 

  • Sohn M, Ho CT (1995) Ammonia generation during thermal degradation of amino acids. J Agric Food Chem 43(12):3001–3003

    Article  CAS  Google Scholar 

  • Suzuki Y, Motoi H, Sato K (1999) Quantitative analysis of pyroglutamic acid in peptides. J Agric Food Chem 47:3248–3251

    Article  CAS  Google Scholar 

  • Swails WS, Bell SJ, Borlase BC, Forse RA, Blackburn GL (1992) Glutamine content of whole proteins: implications for enteral formulas. Nutr Clin Pract 7:77–80

    Article  CAS  Google Scholar 

  • Swaisgood HE (1995) Handbook of milk composition. Academic Press, Boca Raton, pp 465–467

    Google Scholar 

  • The UniProt Knowledgebase (UniProtKB) (2020) www.uniprot.org

  • Tsao M, Otter DE (1999) Quantification of glutamine in proteins and peptides using enzymatic hydrolysis and reversed-phase high-performance liquid chromatography. Anal Biochem 269:143–148

    Article  CAS  Google Scholar 

  • Vendrell J, Aviles FX (1986) Complete amino acid analysis of proteins by dabsyl-derivatization and reversed-phase liquid chromatography. J Chromatogr 358:401–406

    Article  CAS  Google Scholar 

  • Wang X, Liu Y, Li S, Pi D, Zhu H, Hou Y, Shi H, Leng W (2015) Asparagine attenuates intestinal injury, improves energy status and inhibits AMP-activated protein kinase signaling pathways in weaned piglets challenged with Escherichia coli lipopolysaccharide. Br J Nutr 114:553–565

    Article  CAS  Google Scholar 

  • Wilcox PE (1967) Methods in enzymology, vol II. Academic Press, New York, pp 63–76

    Google Scholar 

  • Wu G (2013) Functional amino acids in nutrition and health. Amino Acids 45:407–411

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Division of Abbott Laboratories, Abbott Nutrition, 3300 Stelzer Road, Columbus, OH, 43219, USA

    Paul W. Johns & Steven R. Hertzler

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  1. Paul W. Johns
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  2. Steven R. Hertzler
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Contributions

Steven R. Hertzler: conceptualization, data curation, writing—review and editing. Paul Johns: conceptualization, data curation, formal analysis, validation, methodology, writing—original draft preparation, writing—review and editing.

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Correspondence to Paul W. Johns.

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Steven R. Hertzler declares that he has no conflict of interest. Paul Johns declares that he has no conflict of interest.

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Johns, P.W., Hertzler, S.R. Glutamine and Asparagine in Nutritional Products. Food Anal. Methods 14, 1498–1509 (2021). https://doi.org/10.1007/s12161-021-01978-6

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