CAS 19538-78-4

N-Formyl-L-cysteine

Description:

N-Formyl-L-cysteine is an amino acid derivative characterized by the presence of a formyl group (-CHO) attached to the sulfur-containing amino acid cysteine. This compound is notable for its role in biochemical processes, particularly in the context of protein synthesis and metabolism. It features a thiol (-SH) group, which contributes to its reactivity and ability to form disulfide bonds, essential for protein structure and function. N-Formyl-L-cysteine is typically a white to off-white solid and is soluble in water, making it suitable for various biological applications. Its molecular structure allows it to participate in redox reactions, and it may act as a precursor for other biologically relevant compounds. Additionally, due to the presence of the formyl group, it can engage in further chemical modifications, which can be exploited in synthetic organic chemistry. Overall, N-Formyl-L-cysteine is significant in both biological systems and synthetic applications, highlighting its versatility as a chemical substance.

Formula: C₄H₇NO₃S

InChI: InChI=1S/C4H7NO3S/c6-2-5-3(1-9)4(7)8/h2-3,9H,1H2,(H,5,6)(H,7,8)/t3-/m0/s1

InChI key: InChIKey=JTGVRUVUKGUTRL-VKHMYHEASA-N

SMILES: [C@@H](NC=O)(C(O)=O)CS

Synonyms:

• Cysteine, N-formyl-, L-
• L-Cysteine, N-formyl-
• N-Formyl-L-cysteine
• (2R)-2-Formamido-3-sulfanylpropanoic acid
• N-Formylcysteine

(2R)-2-Formamido-3-sulfanylpropanoic acid

CAS: 19538-78-4

2-Formamido-3-sulfanylpropanoic acid (AFSA) is a reactive intermediate in the synthesis of the amino acids methionine and cysteine. It can react with nucleophiles such as thiols, alcohols, and carboxylic acids. AFSA has been shown to inhibit protein synthesis by acting on nicotinic acetylcholine receptors (nAChRs) in mammalian cells. This inhibition can be reversed by allosteric modulators that increase the activity of nAChRs. AFSA also inhibits the growth of cancer cells by inhibiting the production of growth factors. The acid conjugates of AFSA are thought to be responsible for its anti-inflammatory effects, which have been observed in animal models and human studies.

Formula: C₄H₇NO₃S

Purity: Min. 95%

Molecular weight: 149.17 g/mol

Ref: 3D-UAA53878