N-Terminal Extension of Sweet Peptides in Relation to the Structural Features of Peptide Sweeteners(Organic Chemistry)

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概要

• 論文の詳細を見る

• Sweet aspartyl di- and tripeptide esters were extended toward the N-terminus in relation to the structural features of sweet peptides. The sweet peptides were designed on the basis of the receptor site model. It was found that an extension of the sweet aspartyl dipeptide esters by adding a small D-amino acid residue mostly gave sweet compounds (e.g., D-Ala-L-Asp-D-Ala-OMe), although this significantly decreased their sweetness potencies. Further extension at the N-terminus of the extended sweet tripeptide esters to yield the tetrapeptide esters resulted in a loss of the sweet taste. The N-terminal extension of sweet aspartyl tripeptide esters resulted in faintly sweet or nonsweet tetrapeptide esters. Interestingly, an analogous extension at the N-terminus of the sweet aminomalonyl dipeptide esters gave bitter compounds (e.g., D-Ala-DL-Ama-L-Phe-OMe). These results indicate that the receptor has a small space that can accomodate an additional small D-amino acid residue at the site facing the N-terminus of sweet aspartyl dipentide esters.

• 社団法人日本農芸化学会の論文
• 1990-07-23

著者

• Ota Masafumi

  Central Research Laboratories Ajinomoto Co. Inc.

• Nio Noriki

  Central Research Laboratories, Ajinomoto Co., Inc.

• Ariyoshi Yasuo

  Central Research Laboratories, Ajinomoto Co., Inc.

• HASEGAWA Yasunobu

  Central Research Laboratories, Ajinomoto Co., Inc.

• Nio N

  Ajinomoto Co. Inc. Kanagawa Jpn

• Ariyoshi Y

  Ajinomoto Co. Inc. Kawasaki Jpn

• Ariyoshi Yasuo

  Central Research Laboratories Ajinomoto Co. Inc

• Hasegawa Yasunobu

  Central Research Laboratories Ajinomoto Co. Inc.

関連論文

• Enzymatic Synthesis and Chemical Properties of Sweet Aminomalonyl (Ama) Dipeptide Esters (R)-Ama-(S)-Phe-OMe and (R)-Ama-(S)-Phe-OEt
• N-Terminal Extension of Sweet Peptides in Relation to the Structural Features of Peptide Sweeteners(Organic Chemistry)
• Immobilization of Enzyme in Protein Films Prepared Using Transglutaminase(Food & Nutrition)
• α_-Casein Film Prepared Using Transglutaminase(Food & Nutrition)
• Solid-phase Synthesis and Structure-Taste Relationships of Analogs of the Sweet Protein Monellin
• Highly Probable Active Site of the Sweet Protein Monellin
• Solid-Phase Synthesis of [Asn^]-, [Asn^]-, [Gln^]-, and [Asn^]Monellin, Analogues of the Sweet Protein Monellin
• Solid-Phase Synthesis of Crystalline [Ser^] B-Chain Monellin, an Analogue of the Sweet Protein Monellin(Organic Chemistry)
• Solid-Phase Synthesis of Crystalline Monellin, a Sweet Protein(Organic Chemistry)
• Solid-Phase Synthesis and Crystallization of [Asn^, Gln^, Asn^]-A-Chain-[Asn^, Glu^]-B-Chain-Monellin, an Analogue of the Sweet Protein Monellin(Organic Chemistry)
• Complete Amino Acid Sequence of the Sweet Protein Monellin(Biological Chemistry)
• Solid-Phase Synthesis and Crystallization of Monellin, an Intensely Sweet Protein(Organic Chemistry)
• Inhibition of Angiotensin-Converting Enzyme by Synthetic Peptide Fragments of Various β-Caseins(Biological Chemistry)
• Inhibition of Angiotensin-Converting Enzyme by Synthetic Peptide Fragments of Human κ-Casein(Biological Chemistry)
• Inhibition of Angiotensin-converting Enzyme by Synthetic Peptides of Human β-Casein(Biological Chemistry)
• Location of the Disulfide Bonds of the Sweetness-suppressing Polypeptide Gurmarin
• Functional Properties of Heterologous Polymer Prepared by Transglutaminase between Milk Casein and Soybean Globulin(Food & Nutrition)
• Glutamine-specific Deamidation of α_-Casein by Transglutaminase(Food & Nutrition)
• Gelation of Protein Emulsion by Transglutaminase(Food & Nutrition)
• Inhibition of Prolyl Endopeptidase by Synthetic β-Casein Peptides and Their Derivatives with a C-Terminal Prolinol or Prolinal
• Inhibition of Prolyl Endopeptidase by Synthetic Peptide Fragments of Human β-Casein(Food & Nutrition)
• Functional Properties of Food Proteins Polymerized by Transglutaminase
• Synthesis, Folding, and Biological Activities of Peptide Fragments of Sweet Protein Monellin and Human Cystatin B (Stefin B)
• Solid-Phase Synthesis of Single-Chain Monellin, a Sweet Protein
• Total Synthesis of The Sweet Protein Mabinlin II
• Gelation Mechanism of Protein Solution by Transglutaminase
• The Synthesis of a Sweet Peptide, α-L-Aspartyl-L-phenylalanine Methyl Ester, without the Use of Protecting Groups
• A new synthesis of glutathione via the thiazoline peptide.
• The Reaction of Aspartyl Dipeptide Esters with Ketones
• Studies of Hydroxy Amino Acids. II. The Separation of Diastereoisomers of Hydroxy Amino Acids
• Gelation of Casein and Soybean Globulins by Transglutaminase
• The Convenient Preparation of L-Aspartic Anhydride Hydrochloride and Hydrobromide
• Studies of Hydroxy Amino Acids. I. Separation of Diastereoisomers of Threonine
• Structure-taste relationships of aspartyl tripeptide esters.
• Synthesis of aspartyl pentapeptide esters in relation to structural features of sweet peptides.
• The Structure-Taste Relationships of the Dipeptide Esters Composed of L-Aspartic Acid and β-Hydroxy Amino Acids
• Structure-taste relationships of aspartyl tetrapeptide esters.

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