Bitter Taste of Synthetic C-Terminal Tetradecapeptide of Bovine β-Casein, H-Pro196-Val-Leu-Gly-Pro-Val-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val209-OH, and Its Related Peptides
スポンサーリンク
概要
- 論文の詳細を見る
The primary structure of bovine β-casein contains the partial sequence of-Pro196-Val-Leu-Gly-Pro-Val-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val209 in the C-terminal portion. We previously reported that the synthetic C-terminal octapeptide, Arg202-Val209, is extremely bitter with its threshold value 0.004 mM, 250 times as strong as that of caffeine. To further investigate the bitter taste of the C-terminal portion of β-casein, we synthesized the C-terminal tetradecapeptide, Pro196-Val209, and some of its fragments. A hydrophobic hexapeptide, Pro196-Va201, was twice as bitter as caffeine. The bitter taste of the decapeptide, Pro200-Val209, was the same as that of Arg202-Val209. Although the tetradecapeptide, Pro196-Val209, was composed of two bitter peptides, Pro196-Val201 and Arg202-Val209, its bitter taste was weaker than that of Arg202-Val209 and its threshold value was 0.015 mM. We suggested that the increase of bitterness in peptides through the introduction of hydrophobic amino acids depended on the number of hydrophobic amino acids added. In addition, the synthetic retro analog of Arg202-Val209 (H-Val-Ile-Ile-Pro-Phe-Pro-Gly-Arg-OH) was not as bitter as Arg202-Val209. This indicated that the sequence of Arg202-Val209 is important for extreme bitterness.
- 社団法人 日本農芸化学会の論文
著者
-
Shinoda Ichizo
Department Of Fermentation Technology Faculty Of Engineering Hiroshima University
-
Okai Hideo
Department Of Fermentation Technology Faculty Of Engineering Hiroshima University
-
Fukui Sakuzo
Department Of Bioengineering Faculty Of Engineering Fukuyama University
-
FUSHIMI Akira
Department of Fermentation Technology, Faculty of Engineering, Hiroshima University
-
KATO Hironobu
Department of Fermentation Technology, Faculty of Engineering, Hiroshima University
-
SHINODA Ichizo
Department of Fermentation Technology, Faculty of Engineering, Hiroshima University
関連論文
- Effects of Lactoferrin and Its Peptides on Proliferation of Rat Intestinal Epithelial Cell Line, IEC-18, in the Presence of Epidermal Growth Factor
- Formation of Monohydroxy-n-Nonane-2-Ones from Tricaprin by Fusarium avenaceum f. sp. fabae IFO 7158
- Effects of Lactoferrin and Lactoferricin^ on the Release of Interleukin 8 from Human Polymorphonuclear Leukocytes
- Stimulation by Bovine Lactoferrin of Nerve Growth Factor Synthesis/Secretion in Mouse L-M Cells
- Induction of an Increase in Nerve Growth Factor Content in the Cell-conditioned Medium of Mouse L-M Cells by Basic Peptides
- Peptide Synthesis in Aqueous Solution. V.^ Properties and Reactivities of (p-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification of N-Acylpeptides^
- Role of Basic and Acidic Fragments in Delicious Peptides (Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) and the Taste Behavior of Sodium and Potassium Salts in Acidic Oligopeptides
- Practical Debittering Using Model Peptides and Related Compounds(Food & Nutrition)
- Extracellular Formation of Triglycerides from Glucose by a Mutant Strain of Trichosporon
- Extracellular Production of Palmitoleic Triglycerides by a Yeast, Trichosporon
- Subterminal Hydroxylation of Ketoalkanes by Fungi
- A Novel Enzyme System : The n-Alkane-2-One-Forming Enzyme System in Penicillium decumbens IFO-7091
- Formation of n-Alkane-2-Ones and n-Alkane-2-Ols from Triglycerides by a Black Yeast, Aureobasidium
- Methylalkylketone Fermentation from Palm-Kernel Oil by Penicillium decumbens IFO 7091
- Screening of Methylalkylketone-Accumulating Fungi from Type Culture Strains
- Triglyceride-Binding Proteins in the Culture Fluid of a Triglyceride-Using Fungus Strain, SM-30
- Production of Ketoalkanes from Fatty Acid Esters by a Fungus, Trichoderma
- Characteristics of Lipase Modified with Water-soluble Acylating Reagents and Its Esterification Ability
- Simple Monitoring System for R-Mediated Site-specific Recombination on Chromosomes in Saccharomyces cerevisiae
- Overexpression and Secretion of Cellulolytic Enzymes by δ-Sequence-Mediated Multicopy Integration of Heterologous DNA Sequences into the Chromosomes of Saccharomyces cerevisiae
- Expression of the Carboxymethylcellulase Gene, CMCl, from Cryptococus flavus in Saccharomyces cerevisiae
- Tastes Produced by Peptides Containing Ionic Groups and by Related Compounds
- Further Studies on the Preparation of Low Sodium Chloride-containing Soy Sauce by Using Ornithyltaurine Hydrochloride and Its Related Compounds
- Preparation of Low Sodium Chloride Containing Soy Sauce Using Amino Acid Based Saltiness Enhancers
- Identification of the spoVE Gene Product of Bacillus subtilis(Microbiology & Fermentation Industry)
- Perfect Enantioselective Hydrolysis of Amino Acid Esters by Modified α-Chymotrypsin
- Relationship between Taste and Structure of O-Aminoacyl Sugars Containing Basic Amino Acids
- δ-Acetyl-L-ornithyl-β-alanine Methyl Ester Hydrochloride, an Intermolecule Type Sweetener(Food & Nutrition)
- Mechanism for the Bitter Tasting Potency of Peptides Using O-Aminoacyl Sugars as Model Compounds^+(Food & Nutrition)
- An Enhancing Effect on the Saltiness of Sodium Chloride of Added Amino Acids and Their Esters(Food & Nutrition)
- Glycine Methyl or Ethyl Ester Hydrochloride as the Simplest Examples of Salty Peptides and Their Derivatives(Foof & Nutrition)
- Synthesis of Bitter Peptides Composed of Aspartic Acid and Glutamic Acid(Food & Nutrition)
- Enzymatic Peptide Synthesis with Fatty Acid-modified Chymotrypsin and Trypsin in Aqueous-organic Media
- Enzymatic Functions of Fatty Acid-modified Chymotrypsin and Trypsin in Aqueous-organic Media
- A Mechanism for Bitter Taste Sensibility in Peptides(Food & Nutrition)
- Taste of Proline-containing Peptides(Food & Nutrition)
- Role of the Hydrophobic Amino Acid Residue in the Bitterness of Peptidest(Food & Nutrition)
- Bitterness of Phenylalanine- and Tyrosine-containing Peptides(Food & Nutrition)
- Characteristics of Chymotrypsin Modified with Water-soluble Acylating Reagents and Its Peptide Synthesis Ability in Aqueous Organic Media
- Bitter Taste of H-Pro-Phe-Pro-Gly-Pro-Ile-Pro-OH Corresponding to the Partial Sequence (Positions 61〜67) of Bovine β-Casein, and Related Peptide(Food & Nutrition)
- Characteristic Decrease of Nuclear Protein Kinase Activity in Gl-Arrested Cells of Saccharo-myces cerevisiae cdc28
- Bitterness of Diastereomers of a Hexapeptide (Arg-Arg-Pro-Pro-Phe-Phe) Containing D-Phenylalanine in Place of L-Phenylalanine(Food & Nutrition)
- Bitter Taste of H-Val-Val-Val-Pro-Pro-Phe-Leu-OH Corresponding to the Partial Sequence (Positions 82〜88) of Bovine β-Casein, and Related Peptides(Food & Nutrition)
- Cloning and Molecular Analysis of cDNA Encoding a Carboxymethylcellulase of the Yeast Cryptococcus flavus
- Purification and Characterization of a Carboxymethylcellulose-Degrading Enzyme Secreted by a Yeast Strain Newly Isolated from Soil
- New Taste-blind Substances. Studies on the Sensory Divergence of Bitterness to the Taste-blindness of 2-Mercaptoimidazoline, 2-Mercaptobenzothiazole and Their Derivatives, with Special Reference to Their Molecular Structure
- Variation in Bitterness Potency When Introducing Gly-Gly Residue into Bitter Peptides
- Bitterness of Leucine-containing Peptides
- Cloning of a Gene Coding for Rhodotorucin A, a Farnesyl Peptide Mating Pheromone of Rhodosporidium toruloides(Biological Chemistry)
- A Rapid and Transient Increase of Cellular Ca^ in Response to Mating Pheromone in Saccharomyces cerevisiae(Biological Chemistry)
- Mating Signals Control Expression of both Starch Fermentation Genes and a Novel Flocculation Gene FLO8 in the Yeast Saccharomyces
- The Relationship between Taste and Primary Structure of "Delicious Peptide" (Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from Beef Soup
- Studies of bitter peptides from casein hydrolyzate. X. Synthesis and bitter taste of H-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val-OH corresponding to C-terminal portion of .BETA.-casein.
- Studies of bitter peptides from casein hydrolyzate. IV. Relationship between bitterness and hydrophobic amino acids moiety in the C-terminal of BPIa (Arg-Gly-Pro-Pro-Phe-Ile-Val).
- Studies of bitter peptides from casein hydrolyzate. VII. Bitterness of the retro-BPIa (Val-Ile-Phe-Pro-Pro-Gly-Arg) and its fragments.
- Fluctuation of α-Factor-inactivating Activity during the Cell Division Cycle of Saccharomyces cerevisiae a Cells
- In Vitro Replication of Nuclear Deoxyribonucleic Acid in Isolated Nuclei of Saccharomyces cerevisiae
- In Vitro Deoxyribonucleic-acid-Replicating System Solubilized from Isolated Nuclei of Saccharomyces cerevisiae
- A Study on the Biosynthesis of Tremerogen A-10, a Polyisoprenyl Peptide Mating Pheromone of Tremella mesenterica, Using an Inhibitor of Mevalonate Synthesis
- Peptide synthesis in aqueous solution. III. Synthesis and biological activity of cyclohexylamide derivatives of peptides related to a molluscan neuropeptide, FMRFamide (Phe-Met-Arg-Phe-NH2).
- Cloning and Expression of the Saccharomycopsis fibuligera α-Amylase Gene in Saccharomyces cerevisiae
- Cloning and Expression in Saccharomyces cerevisiae of the Secretable Acid Protease Gene from Saccharomycopsis fibuligera
- Proteolytic Processing of Glucoamylase in the Yeast Saccharomyces diastaticus
- High-frequency Transformation of Saccharomyces cerevisiae with Linear Deoxyribonucleic Acid
- Peptide synthesis in aqueous solution. IV. Preparation and properties of [p-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate(Z-ODSP), [p-(t-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate(Boc-ODSP) and [p-(9-fluorenylmethyloxycarbon
- Bitter Taste of Synthetic C-Terminal Tetradecapeptide of Bovine β-Casein, H-Pro196-Val-Leu-Gly-Pro-Val-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val209-OH, and Its Related Peptides
- An improved resolution of .BETA.-hydroxy-DL-aspartic acid on optically active resin containing L-lysine or L-ornithine.
- Peptide synthesis in aqueous solution. II. Synthesis and biological activity of a molluscan neuropeptide, FMRFamide (Phe-Met-Arg-Phe-NH2) analogs for N-terminal moiety.
- Studies on N-glycopeptides. II. Separation of .ALPHA.- and .BETA.-amide of N-(L-aspartyl)-.BETA.-D-glucopyranosylamine obtained via N-(benzyloxycarbonyl)-L-aspartic anhydride.
- Studies of bitter peptides from casein hydrolyzate. III. Bitter taste of synthetic analogs of BPIa (Arg-Gly-Pro-Pro-Phe-Ile-Val) containing D-proline or glycine in place of L-proline.
- Studies of bitter peptides from casein hydrolyzate. V. Bitterness of the synthetic N-terminal analogs of des-Gly2-BPIa (Arg-Pro-Pro-Phe-Ile-Val).
- Studies of bitter peptides from casein hydrolyzate. IX. Syntheses and bitter taste of bitter peptide BPIa dimer, (Arg-Gly-Pro-Pro-Phe-Ile-Val)2, and Gly-Gly BPIa derivatives.
- Studies on a Model of Bitter Peptides Including Arginine, Proline and Phenylalanine Residues. II.1) Bitterness Behavior of a Tetrapeptide (Arg-Pro-Phe-Phe) and Its Derivatives
- Studies on a Model of Bitter Peptides Including Arginine, Proline and Phenylalanine Residues. I. Bitter Taste of Di- and Tripeptides, and Bitterness Increase of the Model Peptides by Extension of the Peptide Chain
- Methyl 2, 3-Di-O-(L-alanyl)-α-D-glucopyranoside, a New Sweet Substance
- Subunit Structure of Glucoamylase of Saccharomyces diastaticus
- Methyl 2, 3-Di-O-(L-α-aminobutyryl)-α-D-glucopyranoside, a New Sweet Substance, and Tastes of Related Compounds of Neutral Amino Acids and D-Glucose Derivatives
- Preparation of 0-Aminoacyl Sugars as Enzymatically Removable Protections for Hydroxyl Groups in Carbohydrates
- Peptide synthesis in aqueous solution. I. Application of p-dialkyl-sulfoniophenols as a water-soluble coupling reagent.
- Secretion of Saccharomyces diastaticus Glucoamylase from Schizosaccharomyces pombe
- Molecular Cloning of a Glucoamylase-producing Gene in the Yeast Saccharomyces
- Isolation of Glucoamylase-non-producing Mutants in the Yeast Saccharomyces diastaticus
- Subsite structure of Saccharomycopsis .ALPHA.-amylase secreted from Saccharomyces cerevisiae.