Translations:Amino acid/107/en

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Encoded (proteinogenic) amino acids

General topics

By properties

Aliphatic	Branched-chain amino acids (Valine Isoleucine Leucine) Methionine Alanine Proline Glycine
Aromatic	Histidine Tyrosine Tryptophan Phenylalanine
Polar, uncharged	Asparagine Glutamine Serine Threonine
Positive charge (pK_a)	Lysine (≈10.8) Arginine (≈12.5) Histidine (≈6.1) Pyrrolysine
Negative charge (pK_a)	Aspartic acid (≈3.9) Glutamic acid (≈4.1) Selenocysteine (≈5.4) Cysteine (≈8.3) Tyrosine (≈10.1)

Amino acids types: Encoded (proteins)
Essential
Non-proteinogenic
Ketogenic
Glucogenic
Secondary amino
Imino acids
D-amino acids
Dehydroamino acids

Intramolecular
(strong)

Covalent	Electron deficiency 3c–2e 4c–2e 8c–2e Hypervalence 3c–4e Agostic Bent Coordinate (dipolar) Pi backbond Metal–ligand multiple bond Charge-shift Hapticity Conjugation Hyperconjugation Aromaticity homo bicyclo
Metallic	Metal aromaticity
Ionic

Intermolecular
(weak)

Van der Waals forces	London dispersion
Hydrogen	Low-barrier Resonance-assisted Symmetric Dihydrogen bonds C–H···O interaction
Noncovalent other	Mechanical Halogen Chalcogen Metallophilic (aurophilic) Intercalation Stacking Cation–pi Anion–pi Salt bridge

Electron counting rules

Protein primary structure and posttranslational modifications

General

Single specific AAs

Serine/Threonine	Phosphorylation Dephosphorylation Glycosylation O-GlcNAc ADP-ribosylation
Tyrosine	Phosphorylation Dephosphorylation ADP-ribosylation Sulfation Porphyrin ring linkage Adenylylation Flavin linkage Topaquinone (TPQ) formation Detyrosination
Cysteine	Palmitoylation Prenylation
Aspartate	Succinimide formation ADP-ribosylation
Glutamate	Carboxylation ADP-ribosylation Methylation Polyglutamylation Polyglycylation
Asparagine	Deamidation Glycosylation
Glutamine	Transglutamination
Lysine	Methylation Acetylation Acylation Adenylylation Hydroxylation Ubiquitination Sumoylation ADP-ribosylation Deamination Oxidative deamination to aldehyde O-glycosylation Imine formation Glycation Carbamylation Succinylation Lactylation Propionylation Butyrylation
Arginine	Citrullination Methylation ADP-ribosylation
Proline	Hydroxylation
Histidine	Diphthamide formation Adenylylation
Tryptophan	C-mannosylation

Crosslinks between two AAs

Cysteine–Cysteine	Disulfide bond ADP-ribosylation
Methionine–Hydroxylysine	Sulfilimine bond
Lysine–Tyrosine	Lysine tyrosylquinone (LTQ) formation
Tryptophan–Tryptophan	Tryptophan tryptophylquinone (TTQ) formation

Crosslinks between three AAs

Serine–Tyrosine–Glycine	p-Hydroxybenzylidene-imidazolinone (HBI) formation (chromophore)
Histidine–Tyrosine–Glycine	4-(p-hydroxybenzylidene)-5-imidazolinone (HBI) formation (chromophore)
Alanine–Serine–Glycine	Methylidene-imidazolone (MIO) formation

Crosslinks between four AAs

Allysine–Allysine–Allysine–Lysine	Desmosine

Metabolism: Protein metabolism, synthesis and catabolism enzymes

Essential amino acids are in Capitals

LYSINE→	Saccharopine dehydrogenase Glutaryl-CoA dehydrogenase
LEUCINE→	3-Hydroxybutyryl-CoA dehydrogenase Branched-chain amino acid aminotransferase Branched-chain alpha-keto acid dehydrogenase complex Enoyl-CoA hydratase HMG-CoA lyase HMG-CoA reductase Isovaleryl coenzyme A dehydrogenase α-Ketoisocaproate dioxygenase Leucine 2,3-aminomutase Methylcrotonyl-CoA carboxylase Methylglutaconyl-CoA hydratase (See Template:Leucine metabolism in humans – this diagram does not include the pathway for β-leucine synthesis via leucine 2,3-aminomutase)
TRYPTOPHAN→	Indoleamine 2,3-dioxygenase/Tryptophan 2,3-dioxygenase Arylformamidase Kynureninase 3-hydroxyanthranilate oxidase Aminocarboxymuconate-semialdehyde decarboxylase Aminomuconate-semialdehyde dehydrogenase
PHENYLALANINE→tyrosine→	(see below)

G→pyruvate
→citrate

glycine→serine→	Serine hydroxymethyltransferase Serine dehydratase glycine→creatine: Guanidinoacetate N-methyltransferase Creatine kinase
alanine→	Alanine transaminase
cysteine→	D-cysteine desulfhydrase
threonine→	L-threonine dehydrogenase

G→glutamate→
α-ketoglutarate

HISTIDINE→	Histidine ammonia-lyase Urocanate hydratase Formiminotransferase cyclodeaminase
proline→	Proline oxidase Pyrroline-5-carboxylate reductase 1-Pyrroline-5-carboxylate dehydrogenase/ALDH4A1 PYCR1
arginine→	Ornithine aminotransferase Ornithine decarboxylase Agmatinase
→alpha-ketoglutarate→TCA	Glutamate dehydrogenase
Other	cysteine+glutamate→glutathione: Gamma-glutamylcysteine synthetase Glutathione synthetase Gamma-glutamyl transpeptidase glutamate→glutamine: Glutamine synthetase Glutaminase

G→propionyl-CoA→
succinyl-CoA

VALINE→	Branched-chain amino acid aminotransferase Branched-chain alpha-keto acid dehydrogenase complex Enoyl-CoA hydratase 3-hydroxyisobutyryl-CoA hydrolase 3-hydroxyisobutyrate dehydrogenase Methylmalonate semialdehyde dehydrogenase
ISOLEUCINE→	Branched-chain amino acid aminotransferase Branched-chain alpha-keto acid dehydrogenase complex 3-hydroxy-2-methylbutyryl-CoA dehydrogenase
METHIONINE→	generation of homocysteine: Methionine adenosyltransferase Adenosylhomocysteinase regeneration of methionine: Methionine synthase/Homocysteine methyltransferase Betaine-homocysteine methyltransferase conversion to cysteine: Cystathionine beta synthase Cystathionine gamma-lyase
THREONINE→	Threonine aldolase
→succinyl-CoA→TCA	Propionyl-CoA carboxylase Methylmalonyl CoA epimerase Methylmalonyl-CoA mutase

PHENYLALANINE→tyrosine→	Phenylalanine hydroxylase Tyrosine aminotransferase 4-Hydroxyphenylpyruvate dioxygenase Homogentisate 1,2-dioxygenase Fumarylacetoacetate hydrolase tyrosine→melanin: Tyrosinase

G→oxaloacetate

asparagine→aspartate→	Asparaginase/Asparagine synthetase Aspartate transaminase

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