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Amino Acids in Protein Synthesis

There are 20 naturally occurring proteogenic amino acids; it is these amino acids that are combined together to form the polypeptide chains making up the many different peptides and proteins found across all living organisms (Table 1).

There are 3 additional non-canonical proteogenic amino acids (selenocysteine, pyrrolysine, N-formyl methionine) that are synthesized into proteins only by very specific translational mechanisms; for example, N-formyl methionine is the first amino acid in prokaryotic synthesized proteins.

The proteogenic amino acids, involved in the synthesis of proteins in vivo, are known as the α-amino acids and are characterized by having both an amine (NH2) and a carboxylic acid (COOH) group attached to the first (α) carbon. The functionality of the individual amino acid residues is determined by a side-chain group (R’) attached to the same α-carbon.

Characteristic Amino acid Code Side chain (R’) Structure Isoelectric point (pI)
Hydrophobic Phenylalanine Phe (F) -CH2C6H5 Phenylalanine 5.48
Hydrophobic Methionine Met (M) -CH2CH2SCH3 Methionine 5.74
Hydrophobic Tryptophan Trp (W) -CH2C8H6N Tryptophan 5.89
Hydrophobic Valine Val (V) CH(CH3)2 Valine 5.96
Hydrophobic Glycine Gly (G) -H Glycine 5.97
Hydrophobic Leucine Leu (L) -CH2CH(CH3)2 Leucine 5.98
Hydrophobic Alanine Ala (A) -CH3 Alanine 6.00
Hydrophobic Isoleucine Ile (I) -CH(CH3)CH2CH3 Isoleucine 6.02
Hydrophobic Proline Pro (P) -CH2CH2CH2 Proline 6.30
Polar (uncharged) Cysteine Cys (C) -CH2SH Cysteine 5.07
Polar (uncharged) Asparagine Asn (N) -CH2CONH2 Asparagine 5.41
Polar (uncharged) Threonine Thr (T) -CH(OH)CH3 Threonine 5.60
Polar (uncharged) Glutamine Gln (Q) -CH2CH2CONH2 Glutamine 5.65
Polar (uncharged) Tyrosine Tyr (Y) -CH2-C6H4OH Tyrosine 5.66
Polar (uncharged) Serine Ser (S) -CH2OH Serine 5.68
Basic Histidine His (H) -CH2-C3H3N2 Histidine 7.59
Basic Lysine Lys (K) -(CH2)4NH2 Lysine 9.74
Basic Arginine Arg (R) -(CH2)3NH-C(NH)NH2 Arginine 10.76
Acidic Aspartic acid Asp (D) -CH2COOH Aspartic acid 2.77
Acidic Glutamic acid Glu (E) -CH2CH2COOH Glutamic acid 3.22
Table 1: Peptides and proteins found in living organisms.
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