The Influence of High Pressure on the Formation of Diketopiperazines And Pyroglutamate in Peptides and Peptide Esters

Butz, Peter; García, Avelina Fernández; Schneider, T.R.; Stärke, Joachim; Tauscher, B.; Trierweiler, Bernhard

doi:10.1080/08957950212459

Cited by 11 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The influence of pressure treatments on other peptides containing glutamine at the N terminus remains to be investigated and will be the subject of forthcoming works. However, and in contrast to the results presented here, Butz et al (3) showed that peptides containing glutamine at the C terminus are stable after application of pressure combined with temperature, in the same way as they are generally stable in solution, and therefore regularly used as glutamine supplementation. The typical parameters necessary for a pressure pasteurization range from 400 to 700 MPa, at temperatures not higher than 40-50 °C.…”

Section: Discussioncontrasting

confidence: 99%

“…Those reactions might lead to the formation of undesirable compounds and, therefore, should not be disregarded. For instance, it has been reported that high pressure accelerates the formation of a diketopiperazine after hydrolysis of the ester bond at the C terminus of certain peptides (2,3) and induces the cyclization of the amino acid glutamine (4) under neutral or basic pH.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Pressure/Temperature Combined Treatments of Precursors Yield Hormone-like Peptides with Pyroglutamate at the N Terminus

García¹,

Butz²,

Trierweiler³

et al. 2003

J. Agric. Food Chem.

View full text Add to dashboard Cite

Peptides containing the cyclic product of glutamine at the N terminus are usually biologically active. If the cyclization of glutamine was associated with a volume reduction, pressure should displace the equilibrium in the direction of the lower volume. Here, results in model solutions and in whey are discussed, showing that the theorized cyclization of glutamine in Gln-His-ProNH(2) or Gln-Leu-ProNH(2) is significantly accelerated during the application of heat and even more strongly when elevated temperature and pressure combinations are used. The reaction rate depended on the intensity of the pressure treatment, the pH, and the nature of the amino acids adjacent to glutamine. The products of the reaction were identified as thyrotropin-releasing hormone (TRH) and [Leu(2)]TRH. The reported reactions could affect the naturally balanced concentration of short-chain peptides in foods and therefore induce unpredictable biological effects.

show abstract

Section: Discussioncontrasting

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pressure/Temperature Combined Treatments of Precursors Yield Hormone-like Peptides with Pyroglutamate at the N Terminus

García¹,

Butz²,

Trierweiler³

et al. 2003

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…Both degradation products are not sweet, and therefore, high-pressure application of aspartame-containing food products will probably decrease their sweetness. Similar results were reported for leucylleucine methyl ester . Decomposition of this dipeptide into Leu-Leu and the diketopiperazine of Leu-Leu increased with increasing pressure intensity at 60 °C.…”

Section: Degradation Of Peptides Without the Intervention Of Other Re...supporting

confidence: 86%

Chemical Modifications of Peptides and Their Impact on Food Properties

2011

View full text Add to dashboard Cite

Introduction 7876 2. Importance of Peptides in Food 7877 3. Degradation of Peptides without the Intervention of Other Reactive Species 7877 3.1. Peptide Chain Cleavage 7879 3.1.1. Peptide Hydrolysis 7879 3.1.2. Intramolecular Cyclizations in the Peptide Chain 7879 3.2. Peptide Backbone Modifications 7881 3.3. Peptide Side-Chain Modifications 7882 3.4. Peptide Cross-Linking 7883 3.5. Peptide Breakdown 7884 4. Reactions of Peptides with Carbonyl Compounds 7885 4.1. Reactions between Peptides and Carbohydrates 7885 4.1.1. Introduction 7885 4.1.2. Initial Stage of the Maillard Reaction 7885 4.1.3. Advanced Stages of the Maillard Reaction 7887 4.1.3.1. Formation of Color 7888 4.1.3.2. Formation of Taste 7888 4.1.3.3. Formation of Aroma 7888 4.1.3.4. Formation of Biological Activity 7889 4.1.3.5. Formation of Peptide Side-Chain Modifications and Cross-Links 7890 4.2. Reactions between Peptides and Lipids 7893 4.3. Reactions between Peptides and Glyoxal or Methylglyoxal 7896 4.4.

show abstract

“…For instance, it has been reported that high pressure induces the formation of hormone‐like substances after cyclization of glutamine at the N‐terminus of certain peptides (Fernández García and others 2003). The same authors reported that the application of pressure under certain conditions accelerates the formation of diketopiperazines, peptides with biological activity formed from aspartame (Butz and others 1997, 2002).…”

Section: Hormone‐like Peptidesmentioning

confidence: 99%

Formation Risk of Toxic and Other Unwanted Compounds in Pressure‐Assisted Thermally Processed Foods

Segovia-Bravo¹,

Ramírez²,

Durst³

et al. 2011

Journal of Food Science

View full text Add to dashboard Cite

Consumers demand, in addition to excellent eating quality, high standards of microbial and chemical safety in shelf-stable foods. This requires improving conventional processing technologies and developing new alternatives such as pressure-assisted thermal processing (PATP). Studies in PATP foods on the kinetics of chemical reactions at temperatures (approximately 100 to 120• C) inactivating bacterial spores in low-acid foods are severely lacking. This review focuses on a specific chemical safety risk in PATP foods: models predicting if the activation volume value (V a ) of a chemical reaction is positive or negative, and indicating if the reaction rate constant will decrease or increase with pressure, respectively, are not available. Therefore, the pressure effect on reactions producing toxic compounds must be determined experimentally. A recent model solution study showed that acrylamide formation, a potential risk in PATP foods, is actually inhibited by pressure (that is, its V a value must be positive). This favorable finding was not predictable and still needs to be confirmed in food systems. Similar studies are required for other reactions producing toxic compounds including polycyclic aromatic hydrocarbons, heterocyclic amines, N-nitroso compounds, and hormone like-peptides. Studies on PATP inactivation of prions, and screening methods to detect the presence of other toxicity risks of PATP foods, are also reviewed.

show abstract

The Influence of High Pressure on the Formation of Diketopiperazines And Pyroglutamate in Peptides and Peptide Esters

Cited by 11 publications

References 0 publications

Pressure/Temperature Combined Treatments of Precursors Yield Hormone-like Peptides with Pyroglutamate at the N Terminus

Pressure/Temperature Combined Treatments of Precursors Yield Hormone-like Peptides with Pyroglutamate at the N Terminus

Chemical Modifications of Peptides and Their Impact on Food Properties

Formation Risk of Toxic and Other Unwanted Compounds in Pressure‐Assisted Thermally Processed Foods

Contact Info

Product

Resources

About