L-cystathionine

Base Information

• Chemical Name: L-cystathionine
• CAS No.: 56-88-2
• Deprecated CAS: 535-35-3,733035-14-8
• Molecular Formula: C7H14N2O4S
• Molecular Weight: 222.265
• Hs Code.: 29309090
• European Community (EC) Number: 200-295-8
• UNII: 375YFJ481O
• DSSTox Substance ID: DTXSID20971384
• Nikkaji Number: J4.574H
• Wikipedia: Cystathionine
• Wikidata: Q28529685
• NCI Thesaurus Code: C118875
• Metabolomics Workbench ID: 37075
• Mol file: 56-88-2.mol

Synonyms:Cystathionine

Chemical Property of L-cystathionine

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Melting Point: 312
• Refractive Index: 1.592
• Boiling Point: 481 °C at 760 mmHg
• PKA: 2.08±0.10(Predicted)
• Flash Point: 244.7 °C
• PSA: 151.94000
• Density: 1.43 g/cm³
• LogP: 0.33410
• Storage Temp.: −20°C
• Solubility.: Aqueous Acid (Slightly)
• XLogP3: -6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 222.06742811
• Heavy Atom Count: 14
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

L-(+)-Cystathionine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(CSCC(C(=O)O)N)C(C(=O)O)N
• Isomeric SMILES: C(CSC[C@@H](C(=O)O)N)[C@@H](C(=O)O)N
• 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.
• Uses: Intermediate in transsulfuration whereby the mammal transfers the sulfur of methionine via homocysteine to cysteine L-Cystathionine has been used in ultra-performance liquid chromatography for the validation of cystathionine and the correlation of its abundance with vertebrate metamorphosis. It has also been used as an inhibitor of sinusoidal GSH (glutathione) carrier to signify that thiol redox state imbalance is associated with the modulation of autophagy in carcinoma cells.

Technology Process of L-cystathionine

There total 18 articles about L-cystathionine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

Nα-tert-butyloxycarbonylcystathionine α'-methyl ester (75189-61-6) → L-cystathionine (56-88-2)

Guidance literature:

With hydrogenchloride; for 1h; Heating;

Reference yield: 76.0%

(S)-2-amino-4-[(R)-2-amino-2-carboxyethylsulfanyl]butanoic acid dihydrochloride → L-cystathionine (56-88-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 1h; pH=7 - 8;

DOI:10.1080/09168451.2016.1230008

Reference yield: 54.0%

2-amino-3-chloropropanoic acid (2731-73-9) + L-homocysteine thiolactone hydrochloride (31828-68-9) → L-cystathionine (56-88-2)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 22 ℃; for 64h; Inert atmosphere;

DOI:10.1002/asia.201801031

upstream raw materials:

L-serin

L-homocysteine

N-acetylcystein

3-cyano-3-hydroxy-1-propene

Downstream raw materials:

2-Oxobutyric acid

L-Cysteine

L-cystine

L-homocysteine

Refernces

• 1、 -. "NEW METHIONINE METABOLIC PATHWAY INHIBITORS". Paragraph 0113. . Retrieved 2019/08/08.
• 2、 Raftery, Eric D.,Gharkhanian, Eric G.,Ricapito, Nicole G.,McNamara,Deming, Timothy J.. "Influence of Sulfur-Containing Diamino Acid Structure on Covalently Crosslinked Copolypeptide Hydrogels". . p. 3547 - 3553. Retrieved 2018/09/25.