(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+]
• General Description: L-Homocysteine is a sulfur-containing amino acid involved in methylation processes and sulfur metabolism, serving as a substrate for human betaine-homocysteine S-methyltransferase (BHMT), which converts it to L-methionine. Inhibitors targeting BHMT have been studied to understand enzyme function, with findings indicating that structural modifications, particularly the absence of a nitrogen atom in certain analogs, enhance inhibitory potency, suggesting BHMT's sensitivity to specific molecular conformations during substrate binding.

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

meso-homolanthione

D-homocystine

S-benzyl-D-homocysteine

Refernces

Structure-activity study of new inhibitors of human betaine-homocysteine S-methyltransferase

10.1021/jm8015798

The research focuses on the structure-activity study of new inhibitors for human betaine-homocysteine S-methyltransferase (BHMT), an enzyme that catalyzes the transfer of a methyl group from betaine to L-homocysteine, producing dimethylglycine and L-methionine. The purpose of the study was to design and synthesize a series of BHMT inhibitors that mimic the hypothetical transition state of BHMT substrates, with the aim of developing potent and selective inhibitors to better understand the enzyme's role in sulfur metabolism, osmolytic balance, and other physiological functions. The researchers synthesized and tested various compounds, including analogues with NH, N(CH3), or N(CH3)2 groups separated by different spacers from the homocysteine sulfur atom. They found that only certain inhibitors, particularly those without a nitrogen atom in the S-linked alkyl chain, such as (RS,RS)-5-(3-amino-3-carboxypropylthio)-3-methylpentanoic acid and (RS)5-(3-amino-3-carboxypropylthio)-3,3-dimethylpentanoic acid, showed high potency in inhibiting BHMT. The study concluded that BHMT does not tolerate certain betaine mimics, especially the presence of a nitrogen atom, in these inhibitors, which was surprising and suggests potential conformational changes of BHMT upon binding of substrates/products and inhibitors. The chemicals used in the process included various organic compounds, such as gamma-aminobutyrolactone, 3-mercaptopropionic acid, diethyl acetamidomalonate, and a range of other alkylating agents and protected amino acids, as well as reagents for synthesis and deprotection steps.

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