(2S)-2-azaniumyl-4-sulfanylbutanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-4-sulfanylbutanoate
• CAS No.: 6027-13-0
• Molecular Formula: C4H9NO2S
• Molecular Weight: 135.187
• Hs Code.: 29309090
• Mol file: 6027-13-0.mol

Synonyms:homo-cys;(2S)-2-azaniumyl-4-sulfanylbutanoate;L-homocysteine zwitterion;CHEBI:58199

Chemical Property of (2S)-2-azaniumyl-4-sulfanylbutanoate

Chemical Property:

• Appearance/Colour: Colourless or nearly colourless solid
• Melting Point: 232°C
• Refractive Index: 1.5480 (estimate)
• Boiling Point: 299.691 °C at 760 mmHg
• PKA: 2.24±0.10(Predicted)
• Flash Point: 135.048 °C
• PSA: 102.12000
• Density: 1.259 g/cm³
• LogP: 0.41850
• Storage Temp.: ?20°C
• Solubility.: Aqueous Acid (Sparingly, Heated, Sonicated), Water (Slightly, Heated)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 135.03539970
• Heavy Atom Count: 8
• Complexity: 80.6

Purity/Quality:

97% ^*data from raw suppliers

L-Homocysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CS)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: C(CS)[C@@H](C(=O)[O-])[NH3+]
• Uses: L-Homocysteine is the hydrolysis product of adenosine (A280400), a purine nucleoside. Metabolic fate of L-Homocysteine is converted back to L-Methionine( M260440) via tetrahydrofolate. L-homocysteine has been used as a supplement in cell culture media.

Technology Process of (2S)-2-azaniumyl-4-sulfanylbutanoate

There total 32 articles about (2S)-2-azaniumyl-4-sulfanylbutanoate 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: 96.0%

L-homocysteine thiolactone hydrochloride (31828-68-9) → L-homocysteine (6027-13-0)

Guidance literature:

With sodium hydroxide; at 37 ℃; for 0.0833333h;

DOI:10.1021/ja0430200

Reference yield: 93.0%

L-methionine (63-68-3,26062-47-5,58576-49-1) → L-homocysteine (6027-13-0)

Guidance literature:

With ammonia; sodium; at -60 ℃; for 0.5h;

DOI:10.1021/acs.macromol.8b01442

Reference yield: 91.9%

(S)-1,3-thiazane-4-carboxylic acid (147331-83-7) → L-homocysteine (6027-13-0)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; In ethanol; for 1h; Heating;

DOI:10.1246/bcsj.66.536

upstream raw materials:

(2S,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid

D-methionine

D-homocystine

(R)-1,3-thiazane-4-carboxylic acid

Downstream raw materials:

(S)-5’-(S)-(3-amino-3-carboxypropyl)-5’-thioadenosine

(2R,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid

[methyl-13C]-L-methionine

(2S,2'S)-dimethyl 4,4'-disulfanediylbis(2-(2,2,2-trifluoroacetamido)butanoate)

Refernces

• 1、 Jaworski, Allison F.,Aitken, Susan M.. "Exploration of the six tryptophan residues of Escherichia coli cystathionine β-lyase as probes of enzyme conformational change". . p. 138 - 144. Retrieved 2013.
• 2、 Jindal, Ankur,Rajagopal, Sathyanarayanan,Winter, Lucas,Paul, Surojit,Poddar, Ranjana,Brigman, Jonathan,Allan, Andrea M.,Miller, Joshua W.,Jacobsen, Donald W.. "Hyperhomocysteinemia leads to exacerbation of ischemic brain damage: Role of GluN2A NMDA receptors". . p. 287 - 302. Retrieved 2019.
• 3、 -. "Preparation method of N-fluorenylmethoxycarbonyl-S-(4-methoxytribenzyl)-L-homocysteine". Paragraph 0010; 0021; 0025; 0029; 0033. . Retrieved 2019/10/04.