Cystathionine

Cystathionine
Names


IUPAC name S-((R)-2-amino-2-carboxyethyl)-L-homocysteine
Other names L-Cystathionine; S-[(2R)-2-Amino-2-carboxyethyl]-L-homocysteine
Identifiers
CAS Number	56-88-2^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17755^Y
ChEMBL	ChEMBL209241^Y
ChemSpider	388392^N
ECHA InfoCard	100.000.269
KEGG	C00542^Y
MeSH	Cystathionine
PubChem	439258
InChI InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1^N Key: ILRYLPWNYFXEMH-WHFBIAKZSA-N^N InChI=1/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13) Key: ILRYLPWNYFXEMH-UHFFFAOYAH
SMILES C(CSC[C@@H](C(=O)O)N)[C@@H](C(=O)O)N
Properties
Chemical formula	C₇H₁₄N₂O₄S
Molar mass	222.26 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Cystathionine is an intermediate in the synthesis of cysteine.

An excess in the urine is called cystathioninuria.

Biosynthetically, cystathionine is generated from homocysteine and serine by cystathionine beta synthase (upper reaction in the diagram below). It is then cleaved into cysteine and α-ketobutyrate by cystathionine gamma-lyase (lower reaction).

Cysteine metabolism. Cystathionine beta synthase catalyzes the upper reaction and cystathionine gamma-lyase catalyzes the lower reaction.

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid β-hydroxy β-methylbutyric acid β-hydroxy β-methylbutyryl-CoA Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

Other

Cysteine metabolism	Cysteine sulfinic acid

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