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Amino acids


Amino acids are biologically important organic compounds containing amine (-NH2) 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, hydrogen, oxygen, and nitrogen, though other elements are found in the side-chains of certain amino acids. About 500 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 acids comprise the second-largest component (water is the largest) of human muscles, cells and other tissues. Outside proteins, amino acids perform critical roles in processes such as neurotransmitter transport and biosynthesis.

In biochemistry, amino acids having both the amine and the carboxylic acid groups attached to the first (alpha-) carbon atom have particular importance. They are known as 2-, alpha-, or α-amino acids (generic formula H2NCHRCOOH in most cases, where R is an organic substituent known as a "side-chain"); often the term "amino acid" is used to refer specifically to these. They include the 22 proteinogenic ("protein-building") amino acids, which combine into peptide chains ("polypeptides") to form the building-blocks of a vast array of proteins. These are all L-stereoisomers ("left-handed" isomers), although a few D-amino acids ("right-handed") occur in bacterial envelopes, as a neuromodulator (D-serine), and in some antibiotics. Twenty of the proteinogenic amino acids are encoded directly by triplet codons in the genetic code and are known as "standard" amino acids. The other two ("non-standard" or "non-canonical") are selenocysteine (present in many noneukaryotes as well as most eukaryotes, but not coded directly by DNA), and pyrrolysine (found only in some archea and one bacterium). Pyrrolysine and selenocysteine are encoded via variant codons; for example, selenocysteine is encoded by stop codon and SECIS element.N-formylmethionine (which is often the initial amino acid of proteins in bacteria, mitochondria, and chloroplasts) is generally considered as a form of methionine rather than as a separate proteinogenic amino acid. Codon–tRNA combinations not found in nature can also be used to "expand" the genetic code and create novel proteins known as alloproteins incorporating non-proteinogenic amino acids.


Amino Acid 3-Letter 1-Letter Side-chain

class

Side-chain

polarity

Side-chain

charge (pH 7.4)

Hydropathy

index

Absorbance

λmax(nm)

ε at

λmax (mM−1 cm−1)

MW

(Weight)

Occurrence

in proteins

(%)

Alanine Ala A aliphatic nonpolar neutral 1.8 89.094 8.76
Arginine Arg R basic basic polar positive −4.5 174.203 5.78
Asparagine Asn N amide polar neutral −3.5 132.119 3.93
Aspartic acid Asp D acid acidic polar negative −3.5 133.104 5.49
Cysteine Cys C sulfur-containing nonpolar neutral 2.5 250 0.3 121.154 1.38
Glutamic acid Glu E acid acidic polar negative −3.5 147.131 6.32
Glutamine Gln Q amide polar neutral −3.5 146.146 3.9
Glycine Gly G aliphatic nonpolar neutral −0.4 75.067 7.03
Histidine His H basic aromatic basic polar positive(10%)
neutral(90%)
−3.2 211 5.9 155.156 2.26
Isoleucine Ile I aliphatic nonpolar neutral 4.5 131.175 5.49
Leucine Leu L aliphatic nonpolar neutral 3.8 131.175 9.68
Lysine Lys K basic basic polar positive −3.9 146.189 5.19
Methionine Met M sulfur-containing nonpolar neutral 1.9 149.208 2.32
Phenylalanine Phe F aromatic nonpolar neutral 2.8 257, 206, 188 0.2, 9.3, 60.0 165.192 3.87
Proline Pro P cyclic nonpolar neutral −1.6 115.132 5.02
Serine Ser S hydroxyl-containing polar neutral −0.8 105.093 7.14
Threonine Thr T hydroxyl-containing polar neutral −0.7 119.119 5.53
Tryptophan Trp W aromatic nonpolar neutral −0.9 280, 219 5.6, 47.0 204.228 1.25
Tyrosine Tyr Y aromatic polar neutral −1.3 274, 222, 193 1.4, 8.0, 48.0 181.191 2.91
Valine Val V aliphatic nonpolar neutral 4.2 117.148 6.73
21st and 22nd amino acids 3-Letter 1-Letter MW(Weight)
Selenocysteine Sec U 168.064
Pyrrolysine Pyl O 255.313
Ambiguous Amino Acids 3-Letter 1-Letter
Any / unknown Xaa X All
Asparagine or aspartic acid Asx B D, N
Glutamine or glutamic acid Glx Z E, Q
Leucine or Isoleucine Xle J I, L
Hydrophobic Φ V, I, L, F, W, Y, M
Aromatic Ω F, W, Y, H
Aliphatic (Non-Aromatic) Ψ V, I, L, M
Small π P, G, A, S
Hydrophilic ζ S, T, H, N, Q, E, D, K, R
Positively charged + K, R, H
Negatively charged D, E

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Wikipedia

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