Amino acid

File:AminoAcidball.svg

Amino acids are the end product of protein. The general structure of an α-amino acid, with the amino group on the left and the carboxyl group on the right.

Amino acids are the building blocks of proteins. In eukaryotes, there are 20 "standard" amino acids out of which almost all proteins are made.

In organic chemistry, an amino acid is any molecule that has both amine (NH₂+R) and carboxylic acid (C(=O)OH) functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H₂NCHRCOOH, where R is one of many side groups (see diagram).

There are hundreds

Across all forms of life, about 500 amino acids are known. The most important thing that amino acids do is to be part of proteins, which are long chains of amino acids. Every protein has its own sequence of amino acids, and that sequence makes the protein take different shapes, and have different functions. Amino acids are like the alphabet for proteins; even though you only have a few letters, if you connect them, you can make many different sentences.

Nine of the 20 standard amino acids are "essential" amino acids for humans. They cannot be built (synthesised) from other compounds by the human body. They must be taken in as food. Others may be essential for some ages or medical conditions. Essential amino acids may also differ between species. Herbivores have to get their essential amino acids from their diet, which for some is almost entirely grass. Ruminants such as cows get some amino acids via microbes in the first two stomach chambers.

Structure

An amino acid is an organic acid, a kind of organic chemical. It consists of an α-carbon atom that is covalently bonded to four groups.

• a hydrogen atom
• an amino group (-NH₂)
• a carboxyl group (-COOH)
• a variable R group

Every amino acid has at least one amino group (-NH₂) and one carboxyl group (-COOH), except proline.

Gene expression and biochemistry

These are the proteinogenic amino acids, which are the building blocks for proteins. They are produced by cellular machinery coded for in the genetic code of any organism.

Amino Acid	Short	Abbrev.	Codon(s)	Occurrence in human proteins (%)	Essential in humans
Alanine	A	Ala	GCU, GCC, GCA, GCG	7.8	No
Cysteine	C	Cys	UGU, UGC	1.9	Conditionally
Aspartic acid	D	Asp	GAU, GAC	5.3	No
Glutamic acid	E	Glu	GAA, GAG	6.3	Conditionally
Phenylalanine	F	Phe	UUU, UUC	3.9	Yes
Glycine	G	Gly	GGU, GGC, GGA, GGG	7.2	Conditionally
Histidine	H	His	CAU, CAC	2.3	Yes
Isoleucine	I	Ile	AUU, AUC, AUA	5.3	Yes
Lysine	K	Lys	AAA, AAG	5.9	Yes
Leucine	L	Leu	UUA, UUG, CUU, CUC, CUA, CUG	9.1	Yes
Methionine	M	Met	AUG	2.3	Yes
Asparagine	N	Asn	AAU, AAC	4.3	No
Pyrrolysine	O	Pyl	UAG*	0	No
Proline	P	Pro	CCU, CCC, CCA, CCG	5.2	No
Glutamine	Q	Gln	CAA, CAG	4.2	No
Arginine	R	Arg	CGU, CGC, CGA, CGG, AGA, AGG	5.1	Conditionally
Serine	S	Ser	UCU, UCC, UCA, UCG, AGU, AGC	6.8	No
Threonine	T	Thr	ACU, ACC, ACA, ACG	5.9	Yes
Selenocysteine	U	Sec	UGA**	>0	No
Valine	V	Val	GUU, GUC, GUA, GUG	6.6	Yes
Tryptophan	W	Trp	UGG	1.4	Yes
Tyrosine	Y	Tyr	UAU, UAC	3.2	Conditionally
Stop codon†	-	Term	UAA, UAG, UGA††	-	-

* UAG is normally the amber stop codon, but encodes pyrrolysine if a PYLIS element is present.
** UGA is normally the opal (or umber) stop codon, but encodes selenocysteine if a SECIS element is present.
† The stop codon is not an amino acid, but is included for completeness.
†† UAG and UGA do not always act as stop codons (see above).
‡ An essential amino acid cannot be synthesized in humans. It must be supplied in the diet. Conditionally essential amino acids are not normally required in the diet, but must be supplied to populations which do not make enough of it.

To these α-amino acids further in biosynthesis processes appearing non-essential ones are structurally (here by using SMILES notation) related:

OC(=O)C(N)–

• ├ H .. 🅖 Glycine
• ├ C .. 🅐 Alanine
• │├ C .. 2-Aminobutanoic acid
• ││├ C .. Norvaline
• │││├ –2H .. 🅟 Proline (Dehydronorvaline)
• │││├ C .. Norleucine
• ││││└ N .. 🅚 Lysine
• ││││    └ C(=O)C1N=CCC1C .. 🅞 Pyrrolysine
• │││└ NC(=N)N .. 🅡 Arginine
• ││├ C(=O)N .. 🅠 Glutamine
• ││├ C(=O)O .. 🅔 Glutamic acid
• ││├ O .. Homoserine
• ││└ S .. Homocysteine
• ││    └ C .. 🅜 Methionine
• │├ C(C)C .. 🅛 Leucine
• │├ C(=O)N .. 🅝 Asparagine
• │├ C(=O)O .. 🅓 Aspartic acid
• │├ C1=CNC=N1 .. 🅗 Histidine
• │├ c1ccccc1 .. 🅕 Phenylalanine
• │├ c1ccc(O)cc1 .. 🅨 Tyrosine
• │├ C1=CNc2ccccc12 .. 🅦 Tryptophan
• │├ C1=CNc2ccc(O)cc12 .. Oxitriptan
• │├ c(cc1I)cc(I)c1-O-c2cc(I)c(O)c(I)c2 .. Thyroxine
• │├ O .. 🅢 Serine
• │├ S .. 🅒 Cysteine
• │└ [SeH] .. 🅤 Selenocysteine
• ├ C(C)C .. 🅥 Valine
• ├ C(C)O .. 🅣 Threonine
• └ C(C)CC .. 🅘 Isoleucine

Amino Acid Media

• L-amino acid structure.svg

  Structure of a typical L-alpha-amino acid in the "neutral" form

• The 21 proteinogenic α-amino acids found in eukaryotes, grouped according to their side chains' pKa values and charges carried at physiological pH (7.4)

• 

  Functional groups found in histidine (left), lysine (middle) and arginine (right)

• An amino acid in its (1) molecular and (2) zwitterionic forms

• Ionization and Brønsted character of N-terminal amino, C-terminal carboxylate, and side chains of amino acid residues

• Composite of titration curves of twenty proteinogenic amino acids grouped by side chain category

• Amino acids in food and blood.png

  Share of amino acid in various human diets and the resulting mix of amino acids in human blood serum. Glutamate and glutamine are the most frequent in food at over 10%, while alanine, glutamine, and glycine are the most common in blood.

• Strecker amino acid synthesis scheme.svg

  The Strecker amino acid synthesis

• Peptidformationball.svg

  The condensation of two amino acids to form a dipeptide. The two amino acid residues are linked through a peptide bond.