(2S)-2-azaniumyl-4-ethylsulfanylbutanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-4-ethylsulfanylbutanoate
• CAS No.: 13073-35-3
• Molecular Formula: C6H13NO2S
• Molecular Weight: 163.241
• Hs Code.: 2930909090
• Mol file: 13073-35-3.mol

Synonyms:

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

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.000133mmHg at 25°C
• Melting Point: 280 °C (dec.)(lit.)
• Refractive Index: 22 ° (C=1, 1mol/L HCl)
• Boiling Point: 310.391 °C at 760 mmHg
• PKA: 2.23±0.10(Predicted)
• Flash Point: 141.519 °C
• PSA: 88.62000
• Density: 1.164 g/cm³
• LogP: 1.24180
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 163.06669983
• Heavy Atom Count: 10
• Complexity: 102

Purity/Quality:

98% ^*data from raw suppliers

L-Ethionine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCSCCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: CCSCC[C@@H](C(=O)[O-])[NH3+]
• Uses: Ethionine-induced inhibition of protein synthesis and lowering of ATP level in the liver.

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

There total 10 articles about (2S)-2-azaniumyl-4-ethylsulfanylbutanoate 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: 61.0%

L-homocystine (626-72-2,870-93-9,6027-15-2,7093-69-8,462-10-2) + ethyl iodide (75-03-6) → DL-ethionine (13073-35-3)

Guidance literature:

With ammonia; sodium; sodium hydroxide; In water; at -78 ℃;

DOI:10.1002/anie.201308272

Reference yield: 38.0%

N-acetyl-rac-ethionine (57271-88-2) → DL-ethionine (13073-35-3)

Guidance literature:

With potassium dihydrogenphosphate; porcine kidney acylase I; potassium hydroxide; In water; at 40 ℃; pH=7.5 - 8; Inert atmosphere; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/jacs.9b07223

Reference yield:

ethanethiol (75-08-1) + L-3,6-bis(2-chloroethyl)-2,5-diketopiperazine (5394-22-9) → DL-ethionine (13073-35-3)

Guidance literature:

With ammonia; sodium; Erwaermen des Reaktionsprodukts mit wss.HCl;

DOI:10.1021/ja01150a026

upstream raw materials:

S-benzyl-L-homocysteine

ethanethiol

L-3,6-bis(2-chloroethyl)-2,5-diketopiperazine

O-acetyl-L-homoserine

Downstream raw materials:

S-adenosyl-L-ethionine

(R_SS_C)-ethionine sulfoxide

5'-deoxy-5'-(ethylthio)adenosine

N-(((9H-fluoren-9-yl)oxy)carbonyl)-S-ethyl-L-homocysteine

Refernces

• 1、 Gharakhanian, Eric G.,Bahrun, Ehab,Deming, Timothy J.. "Influence of Sulfoxide Group Placement on Polypeptide Conformational Stability". . p. 14530 - 14533. Retrieved 2019.
• 2、 Singh, Shanteri,Zhang, Jianjun,Huber, Tyler D.,Sunkara, Manjula,Hurley, Katherine,Goff, Randal D.,Wang, Guojun,Zhang, Wen,Liu, Chunming,Rohr, Juergen,Van Lanen, Steven G.,Morris, Andrew J.,Thorson, Jon S.. "Facile chemoenzymatic strategies for the synthesis and utilization of S-adenosyl-L-methionine analogues". . p. 3965 - 3969. Retrieved 2014/05/06.