CAS 73804-75-8

alpha-(fluoromethyl)-L-histidine

Description:

Alpha-(fluoromethyl)-L-histidine is an amino acid derivative characterized by the presence of a fluoromethyl group at the alpha position relative to the carboxyl group. This modification can influence its biochemical properties and interactions. The compound is a non-proteinogenic amino acid, meaning it is not commonly found in proteins but can play a role in various biochemical pathways. Its structure includes an imidazole side chain, characteristic of histidine, which can participate in hydrogen bonding and metal ion coordination, potentially affecting enzyme activity and protein structure. The introduction of the fluoromethyl group may enhance lipophilicity and alter the compound's reactivity compared to standard histidine. This compound is of interest in medicinal chemistry and biochemistry for its potential applications in drug design and as a biochemical probe. As with many fluorinated compounds, it may exhibit unique pharmacokinetic properties, making it a subject of study in the development of therapeutics. Safety and handling precautions should be observed due to the presence of fluorine, which can impart different toxicological profiles compared to its non-fluorinated counterparts.

Formula: C₇H₁₀FN₃O₂

InChI: InChI=1/C7H10FN3O2/c8-3-7(9,6(12)13)1-5-2-10-4-11-5/h2,4H,1,3,9H2,(H,10,11)(H,12,13)/t7-/m1/s1

SMILES: C(c1cnc[nH]1)[C@@](CF)(C(=O)O)N

(S)-(+)-a-Fluoromethylhistidine Dihydrochloride (~90%)

Controlled Product

CAS: 73804-75-8

Stability Very Hygroscopic
Applications A histidine carboxylase inhibitor.
References Kirsch, J., et al.: J. Mol. Biol., 174, 497 (1984), Hayashi, H., et al.: J. Biol. Chem., 261, 11003 (1986), Okamoto, A., et al.: J. Biochem., 116, 95 (1994), Sakai, N., et al.: Life Sci., 62, 989 (1998),

Formula: C₇H₁₂Cl₂FN₃O₂

Purity: ~90%

Color and Shape: Neat

Molecular weight: 260.09

Ref: TR-F593660