Tastes and structures of bitter peptide, asparagine-alanine-leucine-proline-glutamate, and its synthetic analogues.

Asn-Ala-Leu-Pro-Glu (NALPE) is a strong bitter peptide with a minimum response threshold (MRT) of 0.074 mM. To elucidate the relationship of spatial structure and bitterness on peptides, NALPE and its analogues, NALPW, NALPS, NALPL, NALPP, NALPD, and NALPR, were synthesized and sensorially evaluated. Structural analysis using computer simulation for each peptide revealed that the presence of a polar group and hydrophobic bitter amino acids, the composition of hydrophobic regions, the spatial orientation of the polar group and hydrophobic regions, and the proximity between polar groups and hydrophobic regions faced within the same plane space may be the major determinants for the taste type and intensity of peptide bitterness.

[1]  Y. Kusakabe,et al.  Regional expression patterns of taste receptors and gustducin in the mouse tongue. , 2003, Biochemical and biophysical research communications.

[2]  James F Battey,et al.  Functional characterization of human bitter taste receptors. , 2007, The Biochemical journal.

[3]  V. Abram,et al.  Isolation of low-molecular-mass hydrophobic bitter peptides in soybean protein hydrolysates by reversed-phase high-performance liquid chromatography☆ , 1995 .

[4]  J. Maga.  Compound structure versus bitter taste , 1990 .

[5]  S. Arai,et al.  Diffusable Bitter Peptides in Peptic Hydrolyzate of Soybean Protein , 1968 .

[6]  C. Tanford.  Contribution of Hydrophobic Interactions to the Stability of the Globular Conformation of Proteins , 1962 .

[7]  T. Fujita,et al.  Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives. , 1987, Journal of medicinal chemistry.

[8]  N. Ryba,et al.  T2Rs Function as Bitter Taste Receptors , 2000, Cell.

[9]  N. Ryba,et al.  Mammalian Sweet Taste Receptors , 2001, Cell.

[10]  E. Kikuchi,et al.  Variation in Bitterness Potency When Introducing Gly-Gly Residue into Bitter Peptides , 1987 .

[11]  I. Kubo.  Structural basis for bitterness based on Rabdosia diterpenes , 1994, Physiology & Behavior.

[12]  C. Brieskorn.  Physiological and therapeutical aspects of bitter compounds , 1990 .

[13]  S. Fukui,et al.  Taste of Proline-containing Peptides , 1988 .

[14]  Jayaram Chandrashekar,et al.  An amino-acid taste receptor , 2002, Nature.

[15]  Thomas Hofmann,et al.  Bitter Taste Receptors for Saccharin and Acesulfame K , 2004, The Journal of Neuroscience.

[16]  R. J. Gardner.  Correlation of bitterness thresholds of amino acids and peptides with molecular connectivity , 1980 .

[17]  M. Behrens,et al.  The human taste receptor hTAS2R14 responds to a variety of different bitter compounds. , 2004, Biochemical and biophysical research communications.

[18]  C. Kim,et al.  Amino acid sequence analysis of bitter peptides from a soybean proglycinin subunit synthesized in Escherichia coli. , 1999, Bioscience, biotechnology, and biochemistry.

[19]  H. Okai,et al.  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) , 1984 .

[20]  Y. Kawamura,et al.  Isolation and Identification of Bitter Peptides of Tryptic Hydrolysate of Soybean 11S Glycinin by Reverse-phase High-performance Liquid Chromatography , 2003 .

[21]  A. Pronin,et al.  Identification of ligands for two human bitter T2R receptors. , 2004, Chemical senses.

[22]  E. Li-Chan,et al.  Quantitative structure-activity relationship study of bitter peptides. , 2006, Journal of agricultural and food chemistry.

[23]  C. Stammer,et al.  Structural correlation between some amides and a taste receptor model , 1989 .

[24]  J. Warthesen,et al.  Mobile Phases in Reverse‐Phase HPLC for the Determination of Bitter Peptides in Cheese , 1996 .

[25]  T. Hata,et al.  Relationship between Bitterness of Peptides and their Chemical Structures , 1972 .

[26]  R. Hayashi,et al.  Isolation of Bitter Peptides from Tryptic Hydrolysate of Casein and their Chemical Structures , 1970 .

[27]  E. Benedetti,et al.  Sweet and bitter taste: Structure and conformations of two aspartame dipeptide analogues , 1995, Journal of peptide science : an official publication of the European Peptide Society.

[28]  S. Fukui,et al.  Bitterness of Leucine-containing Peptides , 1987 .

[29]  K. H. Ney,et al.  Voraussage der Bitterkeit von Peptiden aus deren Aminosäurezu-sammensetzung , 1971 .

[30]  W. Meyerhof,et al.  Elucidation of mammalian bitter taste. , 2005, Reviews of physiology, biochemistry and pharmacology.

[31]  N. Ishibashi,et al.  A Mechanism for Bitter Taste Sensibility in Peptides , 1988 .