beta,beta'-Thiodi-L-alanine

Base Information

• Chemical Name: beta,beta'-Thiodi-L-alanine
• CAS No.: 922-55-4
• Molecular Formula: C6H12 N2 O4 S
• Molecular Weight: 208.238
• Hs Code.: 2930909090
• Mol file: 922-55-4.mol

Synonyms:beta,beta'-Thiodi-L-alanine;L-lanthionine zwitterion;3,3'-thiodi-L-alanine;L-lanthionine dizwitterion;CHEBI:178193;3,3'-thiodi-L-alanine dizwitterion;3,3'-thiobis-L-alanine dizwitterion;beta,beta'-thiodi-L-alanine dizwitterion;S-(2-amino-2-carboxyethyl)-, (R)-L-cysteine;(2R,2'R)-3,3'-sulfanediylbis(2-azaniumylpropanoate)

Chemical Property of beta,beta'-Thiodi-L-alanine

Chemical Property:

• Vapor Pressure: 7.72E-10mmHg at 25°C
• Melting Point: 302℃ (decomposition)
• Refractive Index: 1.606
• Boiling Point: 462.6°C at 760 mmHg
• PKA: 1.75±0.10(Predicted)
• Flash Point: 233.5°C
• PSA: 151.94000
• Density: 1.499g/cm³
• LogP: -0.05600
• Water Solubility.: 1.498g/L(25 oC)
• XLogP3: -5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 208.05177804
• Heavy Atom Count: 13
• Complexity: 168

Purity/Quality:

97% ^*data from raw suppliers

Lanthionine ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)[O-])[NH3+])SCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C([C@@H](C(=O)[O-])[NH3+])SC[C@@H](C(=O)[O-])[NH3+]

Technology Process of beta,beta'-Thiodi-L-alanine

There total 16 articles about beta,beta'-Thiodi-L-alanine 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: 93.0%

L-Cysteine (52-90-4) + (S)-3-amino-2-oxetanone trifluoroacetic acid salt (112839-94-8) → L,L-lanthionine (922-55-4,496-98-0)

Guidance literature:

In water; for 0.666667h; pH = 5.3;

DOI:10.1021/ja00215a038

Reference yield: 64.0%

N,N'-bis(trifluoroacetyl)-L-lanthionine dimethyl ester (26527-25-3) → D,L-Lanthionine (922-55-4,496-98-0)

Guidance literature:

N,N'-bis(trifluoroacetyl)-L-lanthionine dimethyl ester; With sodium hydroxide; In 1,4-dioxane; at 0 - 5 ℃;

With hydrogenchloride; In 1,4-dioxane; water; pH=6;

DOI:10.1016/j.tet.2010.03.091

Reference yield: 55.0%

(R)-3-[(R)-2-Methoxycarbonyl-2-(2,2,2-trifluoro-acetylamino)-ethylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester (26527-25-3) → D,L-Lanthionine (922-55-4,496-98-0)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/asia.201801031

upstream raw materials:

L-Cysteine

N-Acetamidoacrylic acid

D-cysteine

(2S)-2-aziridinecarboxylic acid

Downstream raw materials:

N,N'-dibenzoyl-L-lanthionine

N-benzyloxycarbonyl-L-cysteine

Bis(Fmoc)-cystine

(R)-2-Benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(4-nitro-phenoxycarbonyl)-ethylsulfanyl]-propionic acid 4-nitro-phenyl ester