Structure-CaSR-Activity Relation of Kokumi γ-Glutamyl Peptides
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- Amino Yusuke
- Institute for Innovation, Ajinomoto Co., Inc.
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- Nakazawa Masakazu
- Research Institute for Bioscience Products & Fine Chemicals, Ajinomoto Co., Inc.
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- Kaneko Megumi
- Institute for Innovation, Ajinomoto Co., Inc.
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- Miyaki Takashi
- Institute of Food Research and Technologies, Ajinomoto Co., Inc.
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- Miyamura Naohiro
- Institute of Food Research and Technologies, Ajinomoto Co., Inc.
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- Maruyama Yutaka
- Institute for Innovation, Ajinomoto Co., Inc.
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- Eto Yuzuru
- Institute for Innovation, Ajinomoto Co., Inc.
書誌事項
- タイトル別名
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- Structure–CaSR–Activity Relation of <i>Kokumi</i> γ-Glutamyl Peptides
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説明
<p>Modulation of the calcium sensing receptor (CaSR) is one of the physiological activities of γ-glutamyl peptides such as glutathione (γ-glutamylcysteinylglycine). γ-Glutamyl peptides also possess a flavoring effect, i.e., sensory activity of kokumi substances, which modifies the five basic tastes when added to food. These activities have been shown to be positively correlated, suggesting that kokumi γ-glutamyl peptides are perceived through CaSRs in humans. Our research is based on the hypothesis that the discovery of highly active CaSR agonist peptides will lead to the creation of practical kokumi peptides. Through continuous study of the structure–CaSR–activity relation of a large number of γ-glutamyl peptides, we have determined that the structural requirements for intense CaSR activity of γ-glutamyl peptides are as follows: existence of an N-terminal γ-L-glutamyl residue; existence of a moderately sized, aliphatic, neutral substituent at the second residue in an L-configuration; and existence of a C-terminal carboxylic acid, preferably with the existence of glycine as the third constituent. By the sensory analysis of γ-glutamyl peptides selected by screening using the CaSR activity assay, γ-glutamylvalylglycine was found to be a potent kokumi peptide. Furthermore, norvaline-containing γ-glutamyl peptides, i.e., γ-glutamylnorvalylglycine and γ-glutamylnorvaline, possessed excellent sensory activity of kokumi substances. A novel, practical industrial synthesis of regiospecific γ-glutamyl peptides is also required for their commercialization, which was achieved through the ring opening reaction of N-α-carbobenzoxy-L-glutamic anhydride and amino acids or peptides in the presence of N-hydroxysuccinimide.</p>
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 64 (8), 1181-1189, 2016
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204178968192
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- NII論文ID
- 130005253946
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 027523040
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- PubMed
- 27477658
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可