Amino acid
Amino acids are organic compounds containing amine (-NH) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. The key elements of an amino acid are carbon (C), hydrogen (H), oxygen (O), and nitrogen (N), although other elements are found in the side chains of certain amino acids. About 500 naturally occurring amino acids are known (though only 20 appear in the genetic code) and can be classified in many ways. They can be classified according to the core structural functional groups' locations as alpha- (α-), beta- (β-), gamma- (γ-) or delta- (δ-) amino acids; other categories relate to polarity, pH level, and side chain group type (aliphatic, acyclic, aromatic, containing hydroxyl or sulfur, etc.). In the form of proteins, amino acid residues form the second-largest component (water is the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis.
Coffee bean
Proteins account for 8% to 12% of dried green coffee beans. A majority of the proteins are of the 11-S storage kind (alpha – component of 32 kDa, beta – component of 22 kDa), most of which are degraded to free amino acids during maturation of green coffee beans. Further, 11-S storage proteins are degraded to their individual amino acids under roasting temperature, thus are an additional source of bitter components due to generation of Maillard reaction products. High temperature and oxygen concentration and low pH degrade 11-S storage proteins of green coffee beans to low-molecular-weight peptides and amino acids. The degradation is accelerated in the presence of organic acids such as chlorogenic acids and their derivatives. Other proteins include enzymes, such as catalase and polyphenol oxidase, which are important for the maturation of green coffee beans. Mature coffee contains free amino acids (4.0 mg amino acid/g robusta coffee and up to 4.5 mg amino acid/g arabica coffee). In "Coffea arabica", alanine is the amino acid with the highest concentration, i.e. 1.2 mg/g, followed by asparagine of 0.66 mg/g, whereas in "C. robusta", alanine is present at a concentration of 0.8 mg/g and asparagine at 0.36 mg/g. The free hydrophobic amino acids in fresh green coffee beans contribute to the unpleasant taste, making it impossible to prepare a desirable beverage with such compounds. In fresh green coffee from Peru, these concentrations have been determined as: isoleucine 81 mg/kg, leucine 100 mg/kg, valine 93 mg/kg, tyrosine 81 mg/kg, phenylalanine 133 mg/kg. The concentration of gamma-aminobutyric acid (a neurotransmitter) has been determined between 143 mg/kg and 703 mg/kg in green coffee beans from Tanzania. Roasted coffee beans do not contain any free amino acids; the amino acids in green coffee beans are degraded under roasting temperature to Maillard products (reaction products between the aldehyde group of sugar and the alpha-amino group of the amino acids). Further, diketopiperazines, e.g. cyclo(proline-proline), cyclo(proline-leucine), and cyclo(proline-isoleucine), are generated from the corresponding amino acids, and are the major source of the bitter taste of roasted coffee. The bitter flavor of diketopiperazines is perceptible at around 20 mg/liter of water. The content of diketopiperazines in espresso is about 20 to 30 mg, which is responsible for its bitterness.