Tastes and Structures of Bitter Peptide, Asparagine-Alanine-Leucine-Proline-Glutamate, and Its Synthetic Analogues

Abstract

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.

Enzymatic hydrolysis of lupin protein isolates—Changes in the molecular weight distribution, technofunctional characteristics, and sensory attributes

“…In addition, it appears that the peptide sequence, volume, and spatial structure also exert an effect on the perception of bitter taste (Kim, Yukio, Kim, & Lee, ). As the peptide length has been shown to increases, the bitterness is enhanced as the larger peptide chain length can increase the interactions with bitter receptors (Fu et al, ; Kim et al, ). Moreover, small hydrophobic peptides may lead to bitterness of protein hydrolysates (Matoba & Hata, ).…”

Enzyme assisted degradation of potential soy protein allergens with special emphasis on the technofunctionality and the avoidance of a bitter taste formation

“…Hydrophobicity, primary sequence, spatial structure, molecular weight, and bulkiness of peptides have been studied as possible influences in bitter taste of hydrolysates (Kim, Kawamura, Kim, & Lee, 2008). Several research groups found that Alcalase has the tendency to hydrolyze at hydrophobic amino acid residues, which cause a high bitterness (Adler-Nissen, 1986;Ishibashi et al, 1988).…”

Flaxseed (Linum usitatissimum L.) oil processing and selected products

“…The presence of proline residues has been found to be a major contributor to peptide bitterness (Ishibashi et al, 1988). It has recently been demonstrated that bitterness is determined by polarity, hydrophobicity, and the spatial structure of the peptides (Kim, Yukio, Kim, & Lee, 2008).…”