CAS 4817-95-2

N-[(Phenylmethoxy)carbonyl]-L-valyl-L-phenylalanine methyl ester

Description:

N-[(Phenylmethoxy)carbonyl]-L-valyl-L-phenylalanine methyl ester, with CAS number 4817-95-2, is a synthetic compound that belongs to the class of amino acid derivatives. This substance features a phenylmethoxycarbonyl group, which enhances its stability and solubility, making it useful in various biochemical applications. The presence of the L-valyl and L-phenylalanine residues contributes to its potential as a peptide mimic, which can be important in drug design and development. The methyl ester functionality indicates that it can undergo hydrolysis to release the corresponding amino acids, which may be relevant in biological systems. This compound is typically characterized by its molecular structure, which includes aromatic rings that can influence its interactions with biological targets. Additionally, it may exhibit specific optical activity due to the presence of chiral centers, making it of interest in studies involving stereochemistry. Overall, its unique structural features make it a valuable compound in medicinal chemistry and peptide synthesis.

Formula: C₂₃H₂₈N₂O₅

InChI: InChI=1S/C23H28N2O5/c1-16(2)20(25-23(28)30-15-18-12-8-5-9-13-18)21(26)24-19(22(27)29-3)14-17-10-6-4-7-11-17/h4-13,16,19-20H,14-15H2,1-3H3,(H,24,26)(H,25,28)/t19-,20-/m0/s1

InChI key: InChIKey=LCLXBNDAOUUZSN-PMACEKPBSA-N

SMILES: [C@@H](CC1=CC=CC=C1)(NC([C@@H](NC(OCC2=CC=CC=C2)=O)[C@H](C)C)=O)C(OC)=O

Synonyms:

• <span class="text-smallcaps">L</smallcap>-Phenylalanine, N-[(phenylmethoxy)carbonyl]-<smallcap>L</span>-valyl-, methyl ester
• <span class="text-smallcaps">L</smallcap>-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-<smallcap>L</span>-valyl]-, methyl ester
• Alanine, N-(N-carboxy-<span class="text-smallcaps">L</smallcap>-valyl)-3-phenyl-, N-benzyl methyl ester, <smallcap>L</span>-
• N-(Benzyloxycarbonyl)-<span class="text-smallcaps">L</smallcap>-valyl-<smallcap>L</span>-phenylalanine methyl ester
• N-(Benzyloxycarbonyl)valylphenylalanine methyl ester
• N-[(Phenylmethoxy)carbonyl]-<span class="text-smallcaps">L</smallcap>-valyl-<smallcap>L</span>-phenylalanine methyl ester
• Z-Val-Phe-OMe
• Alanine, N-(N-carboxy-L-valyl)-3-phenyl-, N-benzyl methyl ester, L-
• L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-L-valyl-, methyl ester
• N-(Benzyloxycarbonyl)-L-valyl-L-phenylalanine methyl ester
• L-Phenylalanine, N-[N-[(phenylmethoxy)carbonyl]-L-valyl]-, methyl ester

Z-Val-Phe-OMe

CAS: 4817-95-2

Z-Val-Phe-OMe is an efficient method for the synthesis of a benzyl ester, which is a precursor to the anti-leishmanial drug Z-Val-Phe. The reaction is carried out in chloroform in the presence of ethyl or benzyl esters and ammonium chloride. This methodology was developed to provide a systematic approach to synthesize this compound. The reaction proceeds through a serine protease catalyzed hydrolysis of the amide bond on the surface of leishmania. Kinetic data shows that Z-Val-Phe-OMe has an IC50 value of 0.87 μM for leishmania and is more active than Z-Val-Phe against L. major, L. mexicana, and L. braziliensis strains.

Formula: C₂₃H₂₈N₂O₅

Purity: Min. 95%

Molecular weight: 412.48 g/mol

Ref: 3D-FV111532