Translations:Amino acid/107/en

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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)

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

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

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

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)

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

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

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

asparagine→aspartate→	Asparaginase/Asparagine synthetase Aspartate transaminase