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Cystathionine

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Cystathionine
Skeletal formula of cystathionine
Ball-and-stick model of the cystathionine molecule as a zwitterion
Names
IUPAC name
2-amino-4-(2-amino-2-carboxy-ethyl) thio-butanoic acid
Other names
L-Cystathionine; S-[(2R)-2-Amino-2-carboxyethyl]-L-homocysteine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.269 Edit this at Wikidata
KEGG
MeSH Cystathionine
  • 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
  • C(CSC[C@@H](C(=O)O)N)[C@@H](C(=O)O)N
Properties
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 checkY☒N ?)

Cystathionine is an intermediate in the synthesis of cysteine.

An excess in the urine is called cystathioninuria.

Biosynthetically, cystathionineis 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.