CAS 3183-08-2

S-(2-amino-2-carboxyethyl)-DL-cysteine

Description:

S-(2-amino-2-carboxyethyl)-DL-cysteine, also known as DL-thiocysteine, is a sulfur-containing amino acid derivative characterized by the presence of both amino and carboxyl functional groups, which contribute to its properties as a zwitterion at physiological pH. This compound features a thiol (-SH) group, which is reactive and plays a crucial role in various biochemical processes, including protein synthesis and redox reactions. It is soluble in water, making it suitable for biological applications. The presence of both the amino and carboxyl groups allows it to participate in peptide bond formation, while the thiol group can form disulfide bonds, influencing protein structure and function. S-(2-amino-2-carboxyethyl)-DL-cysteine is often studied in the context of its potential antioxidant properties and its role in cellular metabolism. As with many amino acids, it can exist in different stereoisomeric forms, with the DL designation indicating a racemic mixture of the D- and L-enantiomers. Its CAS number, 3183-08-2, is used for identification in chemical databases and regulatory contexts.

Formula: C₆H₁₂N₂O₄S

InChI: InChI=1/C6H12N2O4S/c7-3(5(9)10)1-8-4(2-13)6(11)12/h3-4,8,13H,1-2,7H2,(H,9,10)(H,11,12)/t3?,4-/m1/s1

InChI key: InChIKey=DWPCPZJAHOETAG-SEFKMRKONA-N

SMILES: [C@@H](C(O)=O)(CSC[C@@H](C(O)=O)N)N

Synonyms:

• 2-amino-3-[[(1S)-2-hydroxy-2-oxo-1-(sulfanylmethyl)ethyl]amino]propanoic acid
• <span class="text-smallcaps">D</span>-Cysteine, S-[(2S)-2-amino-2-carboxyethyl]-, rel-
• <span class="text-smallcaps">DL</span>-Cysteine, S-(2-amino-2-carboxyethyl)-
• <span class="text-smallcaps">DL</span>-Lanthionine
• Alanine, 3,3'-thiodi-, DL-
• Alanine, 3,3′-thiodi-, <span class="text-smallcaps">DL</span>-
• Cysteine, S-(2-amino-2-carboxyethyl)-
• DL-Cysteine, S-(2-amino-2-carboxyethyl)-
• DL-Lanthionine
• Lanthionine
• S-(2-amino-2-carboxyethyl)cysteine
• rel-S-[(2S)-2-Amino-2-carboxyethyl]-<span class="text-smallcaps">D</span>-cysteine
• D-Cysteine, S-[(2S)-2-amino-2-carboxyethyl]-, rel-
• rel-S-[(2S)-2-Amino-2-carboxyethyl]-D-cysteine
• S-(2-Amino-2-carboxyethyl)-DL-cysteine
• LANTHIONINE, 98%, MIXTURE OF DL AND MESO
• DL-3,3μ-Thiodialanine, S-(2-Amino-2-carboxyethyl)-DL-cysteine
• 3,3'-THIOBIS(2-AMINOPROPIONIC ACID)
• 3,3'-THIODIALANINE
• di(2-amino-2-carboxyethyl) sulphide
• DL-(RG)
• lanthionine, mixture of dl and meso

DL-Lanthionine

CAS: 3183-08-2

Ref: 7W-GM5670

DL-Lanthionine DiTrifluoroacetate

CAS: 3183-08-2

Formula: C₆H₁₂N₂O₄S·2C₂HF₃O₂

Color and Shape: White To Off-White Solid

Molecular weight: 208.23 2*114.02

Ref: 4Z-L-118007

DL-Lanthionine

Controlled Product

CAS: 3183-08-2

Applications DL-Lanthionine is a thioether-amino acid which when present in peptides results in antimicrobial activity. Peptides with this amino acid within it become part of a group named lantibiotics.
References Lohans, C, et al.: J. Am. Chem. Sic., 136, 13150 (2014);

Formula: C₆H₁₂N₂O₄S

Color and Shape: Neat

Molecular weight: 208.24

Ref: TR-L175060