Abstract:
:Oxidative stress, an excess of reactive oxygen species (ROS), may lead to oxidative post-translational modifications of proteins resulting in the cleavage of the peptide backbone, known as α-amidation, and formation of fragments such as peptide amides and α-ketoacyl peptides (α-KaP). In this study, we first compared different approaches for the synthesis of different model α-KaP and then investigated their stability compared to the corresponding unmodified peptides. The stability of peptides was studied at room temperature or at temperatures relevant for food processing (100 °C for cooking and 150 °C as a simulation of roasting) in water, in 1% (m/v) acetic acid or as the dry substance (to simulate the thermal treatment of dehydration processes) by HPLC analysis. Oxidation of peptides by 2,5-di-tert-butyl-1,4-benzoquinone (DTBBQ) proved to be the most suited method for synthesis of α-KaPs. The acyl side chain of the carbonyl-terminal α-keto acid has a crucial impact on the stability of α-KaPs. This carbonyl group has a catalytic effect on the hydrolysis of the neighboring peptide bond, leading to the release of α-keto acids. Unmodified peptides were significantly more stable than the corresponding α-KaPs. The possibility of further degradation reactions was shown by the formation of Schiff bases from glyoxylic or pyruvic acids with glycine and proven through detection of transamination products and Strecker aldehydes of α-keto acids by HPLC-MS/MS. We propose here a mechanism for the decomposition of α-ketoacyl peptides.
journal_name
Amino Acidsjournal_title
Amino acidsauthors
Sajapin J,Hellwig Mdoi
10.1007/s00726-020-02902-8subject
Has Abstractpub_date
2020-10-01 00:00:00pages
1425-1438issue
10eissn
0939-4451issn
1438-2199pii
10.1007/s00726-020-02902-8journal_volume
52pub_type
杂志文章相关文献
AMINO ACIDS文献大全abstract::In an attempt to increase our knowledge regarding the mechanisms of surfactant membrane interaction, we studied the action of several anionic and cationic amino acid-based surfactants on membrane fluidity using fluorescence anisotropy. Anisotropy measurements demonstrated that almost all of the surfactants studied dis...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-006-0447-2
更新日期:2007-09-01 00:00:00
abstract::The regulation of the expression of indoleamine 2,3-dioxygenase (IDO) was studied in cloned murine macrophages (MT2) and microglial (N11) cells. Both cell lines express IDO and inducible nitric oxide synthase activity after interferon-gamma (IFN-gamma) stimulation. The regulation of IDO expression appears to differ in...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/BF01345271
更新日期:1998-01-01 00:00:00
abstract::Two experiments were conducted to evaluate the effects of dietary supplementation with Astragalus polysaccharide (APS) on growth performance, apparent ileal digestibilities (AID) of amino acids (AA), and their serum concentrations in early weaned piglets. In Exp. 1, 60 pigs were weaned at 21 days of age (BW 7.35 +/- 0...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-008-0142-6
更新日期:2009-07-01 00:00:00
abstract::Spermine oxidase (SMO) was discovered much more recently than other enzymes involved in polyamine metabolism; this review summarizes 10 years of researches on this enzyme. Spermine oxidase (SMO) is a FAD-dependent enzyme that specifically oxidizes spermine (Spm) and plays a dominant role in the highly regulated mammal...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-011-1014-z
更新日期:2012-02-01 00:00:00
abstract::Taurine chloramine (TauCl), a product of neutrophil myeloperoxidase - halide system, formed by a reaction of taurine with HOCl, is known as an anti-microbial and anti-inflammatory long-lived oxidant. We previously reported that TauCl inhibits in vitro the production of proinflammatory cytokines (IL-6, IL-8) by RA syno...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-002-0207-x
更新日期:2002-01-01 00:00:00
abstract::In a previous research, we have shown that adequate levels of polyamines are required in transformed mouse fibroblasts for the correlated activations of MAPK subtypes (ERK and JNK) and caspases induced by etoposide and leading to apoptosis. We report now that the treatment of fibroblasts with etoposide also elicited a...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-004-0101-9
更新日期:2004-10-01 00:00:00
abstract::Thrombin, the most potent physiological platelet agonist interacts with cells through a specific G protein-coupled receptor which has been cloned and sequenced. Synthetic thrombin receptor peptides (TRAPs) comprising the first 5 amino acids (SFLLR and SFLLR-NH2) of the new N-terminus tethered ligand of the thrombin re...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/BF01318860
更新日期:1998-01-01 00:00:00
abstract::Interplay between proteins, nucleic acids, carbohydrates and/or lipids is involved in almost every process in life on earth. As a consequence, a wide range of diseases results from abnormal interactions of such biomolecules. The main motivation of foldamer science is the development of scaffolds that are capable of ad...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-011-0894-2
更新日期:2011-08-01 00:00:00
abstract::Increased intracellular cysteine poses a potential danger to cells due to the high ability of cysteine to reduce free iron and promote the Fenton reaction. Here, we studied ways to maintain cysteine homeostasis in E. coli cells while inhibiting protein synthesis with valine or chloramphenicol. When growing wild-type b...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-019-02795-2
更新日期:2019-11-01 00:00:00
abstract::Changes in plasma aromatic amino acids (AAA = phenylalanine, tryptophan, tyrosine) and branched chain amino acids (BCAA = isoleucine, leucine, valine) levels possibly influencing intracranial pressure (ICP) and cerebral oxygen consumption (SjvO(2)) were investigated in 19 sedated patients up to 14 days following sever...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-1202-x
更新日期:2012-09-01 00:00:00
abstract::The Disrupted-in-schizophrenia 1 (DISC1) gene is involved in vulnerability to neuropsychiatric disorders. Naples high-excitability (NHE) rat model neuropsychiatric problems characterized by an unbalanced mesocortical dopamine system. Here, we assessed behavioral and neurochemical effects of immunization against multim...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-014-1897-6
更新日期:2015-03-01 00:00:00
abstract::This study aimed to investigate the ability of curcumin to convert asparagine into acrylamide during heating at different temperatures. Binary and ternary model systems of asparagine-curcumin and asparagine-curcumin-fructose were used to determine the role of curcumin on acrylamide formation in competitive and uncompe...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-1179-5
更新日期:2013-06-01 00:00:00
abstract::When considering protein phosphorylation in bacteria, phosphorylation of aspartic acid and histidine residues mediated by the two-component systems is the first to spring to mind. And yet other phosphorylation systems have been described in bacteria in the past 20 years including eukaryotic-like serine/threonine kinas...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-009-0237-8
更新日期:2009-09-01 00:00:00
abstract::Mice over-expressing the creatine transporter have elevated myocardial creatine levels [Cr] and are protected against ischaemia/reperfusion injury via improved energy reserve. However, mice with very high [Cr] develop cardiac hypertrophy and dysfunction. To investigate these contrasting effects, we applied a non-biase...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-016-2236-x
更新日期:2016-08-01 00:00:00
abstract::This work deals with the Dakin-West synthesis, starting from the nucleoamino acid 1-thyminyl acetic acid, as well the NMR, ESI MS, and X-ray characterization of a heteroaromatic compound denominated by us T(2)CO, comprising two thymine moieties anchored to a 2-propanonic unit, the spectroscopic properties of which wer...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-012-1237-7
更新日期:2012-10-01 00:00:00
abstract::Reports on nucleobase-containing chiral peptides (both natural and artificial) and achiral pseudopeptides are reviewed. Their synthesis, structural features, DNA and RNA-binding ability, as well as some other interesting applications which make them promising diagnostic/therapeutic agents of great importance in many a...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-010-0567-6
更新日期:2010-06-01 00:00:00
abstract::The human organism is exposed to numerous processes that generate reactive oxygen species (ROS). ROS may directly or indirectly cause oxidative modification and damage of proteins. Protein oxidation is regarded as a crucial event in the pathogenesis of various diseases ranging from rheumatoid arthritis to Alzheimer's ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-005-0203-z
更新日期:2005-12-01 00:00:00
abstract::Immobilization of papain on Sepharose 6B in the presence of different concentrations of cysteine affected the enzyme activity depending on cysteine concentration. The maximum specific activity was observed when papain was immobilized with 200 mM cysteine. The immobilization process brought significant enhancement of s...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-009-0302-3
更新日期:2010-03-01 00:00:00
abstract::The coupling between G protein-coupled receptors (GPCRs) and guanine nucleotide-binding proteins (G proteins) regulates various signal transductions from extracellular space into the cell. However, the coupling mechanism between GPCRs and G proteins is still unknown, and experimental determination of their coupling sp...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-1133-6
更新日期:2012-08-01 00:00:00
abstract::Transglutaminases are confounding enzymes which are known to play key roles in various cellular processes. In this paper, we aim to bring together several pieces of evidence from published research and literature that suggest a potentially vital role for transglutaminases in receptor tyrosine kinases (RTK) signalling....
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-011-1113-x
更新日期:2013-01-01 00:00:00
abstract::Relaxin family peptides perform a variety of biological functions by binding and activating relaxin family peptide receptor 1-4 (RXFP1-4), four A-class G protein-coupled receptors. In the present work, we developed a novel ligand binding assay for RXFP3 and RXFP4 based on NanoLuc complementation technology (NanoBiT). ...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-018-2588-5
更新日期:2018-08-01 00:00:00
abstract::Two synthetic routes to bis-armed-alpha-amino acid derivatives are described. The first route involves alkylation of dibromo derivatives with ethyl isocyanoacetate under phase-transfer catalysis (PTC) conditions. The second route uses a palladium-mediated Suzuki-Miyaura cross-coupling reaction between a DL-4-boronophe...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-006-0402-2
更新日期:2007-01-01 00:00:00
abstract::Branched Chain Amino Acids (BCAAs) are related to different aspects of diseases like pathogenesis, diagnosis and even prognosis. While in some diseases, levels of all the BCAAs are perturbed; in some cases, perturbation occurs in one or two while the rest remain unaltered. In case of ischemic heart disease, there is a...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-015-1994-1
更新日期:2015-10-01 00:00:00
abstract::In order to adapt to ever changing environmental conditions, bacteria sense environmental stimuli, and convert them into signals that are transduced intracellularly. Several mechanisms have evolved by which receptors transmit signals across the cytoplasmic membrane. Stimulus perception may trigger receptor dimerizatio...
journal_title:Amino acids
pub_type: 杂志文章,评审
doi:10.1007/s00726-009-0235-x
更新日期:2009-09-01 00:00:00
abstract::The isolated single organotypic slice model allows to investigate the effects of drugs and toxins on the expression of transcription factors in the striatum without dopaminergic and glutamatergic interactions. In this study the effects of margatoxin and iberiotoxin on the expression of c-fos mRNA by in situ hybridizat...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s007260070030
更新日期:2000-01-01 00:00:00
abstract::L-tryptophan (TRP) is the precursor amino acid for the synthesis of serotonin (5-HT). 5-HT is effective both on the food intake and gastrointestinal system contractility. The aim of this study was to search the effects of systemic TRP treatment on 5-HT levels of ileum and searching the effect of ileal contractility an...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-006-0339-5
更新日期:2007-01-01 00:00:00
abstract::Glutaryl-CoA dehydrogenase deficiency (GDD), which is one of the most frequent organic acid disorders, is characterized by a specific age- and regional-dependent neuropathology. We hypothesized that the distinct brain damage in GDD could be caused by the main pathologic metabolites, the organic acids glutaric (GA) and...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s007260050003
更新日期:2000-01-01 00:00:00
abstract::In the absence of exogenous Ca(2+) and Mg(2+) and in the presence of EGTA, which favours the release of endogenous Ca(2+), the polyamine spermine is able to stimulate the activity of pyruvate dehydrogenase complex (PDC) of energized rat liver mitochondria (RLM). This stimulation exhibits a gradual concentration-depend...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-008-0099-5
更新日期:2009-03-01 00:00:00
abstract::The streptococcal enzyme that catalyzes the last step in proline biosynthesis was heterologously expressed and the recombinant protein was purified to electrophoretic homogeneity and characterized thoroughly. As for δ1-pyrroline-5-carboxylate reductases from other sources, it was able to use either NADH or NADPH as th...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-011-1077-x
更新日期:2012-07-01 00:00:00
abstract::Recently, we observed that central administration of L-arginine attenuated stress responses in neonatal chicks, but the contribution of nitric oxide (NO) to this response was minimal. The sedative and hypnotic effects of L-arginine may be due to L-arginine itself and/or its metabolites, excluding NO. To clarify the me...
journal_title:Amino acids
pub_type: 杂志文章
doi:10.1007/s00726-007-0617-x
更新日期:2008-06-01 00:00:00