| Identification | Back Directory | [Name]
L-CYSTATHIONINE | [CAS]
56-88-2 | [Synonyms]
L-CYSTATHIONINE
CYSTATHIONINE, L-
L(+)CYSTATHIONINE
L-CYSTATHIONINE, >= 98% (TLC)
CYSTATHIONINE, L-(DS)(REQUEST QUOTE)
(2R,7S)-2,7-Diamino-4-thiaoctanedioic acid
S-[(R)-2-Amino-2-carboxyethyl]-L-homocysteine
[R]-S-[2-AMINO-2-CARBOXYETHYL]-L-HOMOCYSTEINE
S-[(2R)-2-AMino-2-carboxyethyl]-L-hoMocysteine
L-Cystathionine,(R)-S-(2-Amino-2-carboxyethyl)-L-homocysteine
(2S)-2-Amino-4-{[(2R)-2-amino-2-carboxyethyl]thio}butanoic acid
[R-(R*,S*)]-2-AMino-4-[(2-aMino-2-carboxyethyl)thio]butanoic Acid
(2S)-2-amino-4-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanylbutanoic acid | [EINECS(EC#)]
200-295-8 | [Molecular Formula]
C7H14N2O4S | [MDL Number]
MFCD00036685 | [MOL File]
56-88-2.mol | [Molecular Weight]
222.26 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
312 | [alpha ]
D20 +23.7° (1N HCl) | [density ]
1.430±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
−20°C | [solubility ]
Aqueous Acid (Slightly) | [Boiling point ]
481.0±45.0 °C(Predicted) | [form ]
Solid | [pka]
2.08±0.10(Predicted) | [color ]
White to Off-White | [Optical Rotation]
+26.425 (1 mol dm-3 HCl) | [Merck ]
13,2807 | [BRN ]
2505200 | [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 | [InChIKey]
ILRYLPWNYFXEMH-WHFBIAKZSA-N | [SMILES]
N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
Intermediate in transsulfuration whereby the mammal transfers the sulfur of methionine via homocysteine to cysteine | [Description]
L-(+)-Cystathionine is a dipeptide formed by serine and homocysteine. Transsulfuration of methionine yields homocysteine, which combines with serine to form this precursor of cysteine. L-(+)-Cystathionine is largely expressed in the mammalian brain and deficiency can indicate the presence of metabolic disorders such as cystathioninuria. | [Definition]
ChEBI: L-cystathionine is a modified amino acid generated by enzymic means from L-homocysteine and L-serine. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a tautomer of a L-cystathionine dizwitterion. | [Biochem/physiol Actions]
L-Cystathionine is an intermediate in the biosynthesis of L-cysteine and methionine. It is used as a substrate to differentiate and analyze cystathionine γ-lyase(s). L-Cystathionine is an important non-protein amino acid and is associated with metabolic disorders. In recent studies, L-cystathionine is believed to be the precursor of cyclic imino acid cyclothionine. Cystathioninuria is characterized with imino acid cyclothionine excretion in the urine. | [Purification Methods]
S,S-Cystathionine is purified by converting it to the HCl salt in 20% HCl and carefully basifying with aqueous NH3 until separation is complete. Filter it off and dry it in a vacuum. It forms prisms from H2O. The dibenzoyl derivative has m 229o (from EtOH). [IR: Greenstein & Winitz Chemistry of the Amino Acids (J Wiley) Vol 3 p2690 1961 and Tallan et al. J Biol Chem 230 707 1958, Synthesis: du Vigneaud et al. J Biol Chem 143 59 1942, Anslow et al. J Biol Chem 166 39 1946.] [Prepn: Weiss & Stekol J Am Chem Soc 73 2497 1951; see also du Vigneaud et al. J Biol Chem 143 60 1942, Biological synthesis: Greenberg Methods Enzymol 5 943 1962, Beilstein 4 IV 3197.] | [References]
[1] FINKELSTEIN J D. The metabolism of homocysteine: pathways and regulation.[J]. European Journal of Pediatrics, 1998, 157 Suppl 2: S40-4. DOI: 10.1007/pl00014300
[2] TAKUYA NISHI. Accumulation of L-cystathionine by an Escherichia coli mutant deficient in cystathionine beta-lyase.[J]. Journal of bioscience and bioengineering, 2002, 94 2: 178-181. DOI: 10.1263/jbb.94.178 |
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