24787-89-1

Basic information

• Product Name: Z-VAL-ALA-OH
• Synonyms: Z-L-VALYL-L-ALANINE;Z-VAL-ALA-OH;Aids006477;Aids-006477;CBz-Val-Ala-h;Carbobenzoxy-L-valyl-L-alanine;N-(Benzyloxycarbonyl)-L-valyl-L-alanine;N-[(Phenylmethoxy)carbonyl]-L-valyl-L-alanine
• CAS NO: 24787-89-1
• Molecular Formula: C₁₆H₂₂N₂O₅
• Molecular Weight: 322.36
• Mol File: 24787-89-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 165 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• Boiling Point: 513.5°Cat760mmHg
• Flash Point: 264.4°C
• Appearance: /
• Density: 1.201
• Storage Temp.: -15°C
• PKA: 3.49±0.10(Predicted)
• CAS DataBase Reference: Z-VAL-ALA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-VAL-ALA-OH(24787-89-1)
• EPA Substance Registry System: Z-VAL-ALA-OH(24787-89-1)

Safety Data

• Hazardous Substances Data: 24787-89-1(Hazardous Substances Data)

Usage

Description

Z-VAL-ALA-OH, also known as Z-Valine-Alanine, is a dipeptide derivative featuring a protected valine and alanine amino acids. It is a white powder with specific chemical properties that make it a valuable compound in the field of pharmaceuticals and biochemistry. The presence of the Z-group (benzyloxycarbonyl) provides protection to the peptide bond, which is crucial for its stability and reactivity in various applications.

Uses

Used in Pharmaceutical Industry:
Z-VAL-ALA-OH is used as a building block for the synthesis of various peptide-based drugs and prodrugs. Its application is primarily due to its ability to provide a stable and protected structure that can be easily incorporated into more complex peptide sequences.
Used in Biochemical Research:
In the field of biochemistry, Z-VAL-ALA-OH serves as a useful reagent for the preparation and biological evaluation of peptide amide conjugates of nucleosides. These conjugates are designed as prodrugs, which are converted to their parent drugs by the action of DPPIV/CD26, an enzyme involved in the regulation of various biological processes.
Used in Drug Development:
Z-VAL-ALA-OH is also utilized in the synthesis and evaluation of diacylhydrazines, which are potential inhibitors of the interleukin-1β converting enzyme (ICE). This enzyme plays a critical role in the activation of interleukin-1β, a pro-inflammatory cytokine involved in the pathogenesis of various diseases. By inhibiting ICE, diacylhydrazines may offer therapeutic benefits in the treatment of inflammatory conditions.

InChI:InChI=1/C16H22N2O4/c1-11(2)14(15(20)17-12(3)9-19)18-16(21)22-10-13-7-5-4-6-8-13/h4-9,11-12,14H,10H2,1-3H3,(H,17,20)(H,18,21)/t12-,14-/m0/s1

Upstream product

• 55739-16-7 Z-L-Val-L-Ala-OEt 
• 56-41-7 L-alanin 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 22221-83-6 benzyloxycarbonyl-L-valyl-L-alanine methyl ester 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 

Downstream Products

• 1115-74-8 Val-Ala 
• 161401-75-8 (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid ethyl ester 
• 161401-80-5 3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester 
• 55739-16-7 Z-L-Val-L-Ala-OEt 
• 161401-76-9 (3S,4R)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-4,5-dihydroxy-pentanoic acid ethyl ester 
• 161401-77-0 2,6-Dichloro-benzoic acid (2R,3S)-3-[(S)-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-4-ethoxycarbonyl-2-hydroxy-butyl ester 
• 1361144-02-6 C₁₆H₂₂N₂O₄S 
• 16816-23-2 N-(benzyloxycarbonyl)-L-leucyl-L-valcyl-L-alanine methyl ester 
• 15136-26-2 (3S,6S)-3-methyl-6-(1-methylethyl)piperazine-2,5-dione 

Relevant articles and documents

Optimization and anti-cancer properties of fluoromethylketones as covalent inhibitors for ubiquitin C-terminal hydrolase L1

The deubiquitinating enzyme (DUB) UCHL1 is implicated in various disease states including neurodegenerative disease and cancer. However, there is a lack of quality probe molecules to gain a better understanding on UCHL1 biology. To this end a study was carried out to fully characterize and optimize the irreversible covalent UCHL1 inhibitor VAEFMK. Structure-activity relationship studies identified modifications to improve activity versus the target and a full cellular characterization was carried out for the first time with this scaffold. The studies produced a new inhibitor, 34, with an IC50 value of 7.7 μM against UCHL1 and no observable activity versus the closest related DUB UCHL3. The molecule was also capable of selectively inhibiting UCHL1 in cells and did not demonstrate any discernible off-target toxicity. Finally, the molecule was used for initial probe studies to assess the role of UCHL1 role in proliferation of myeloma cells and migration behavior in small cell lung cancer cells making 34 a new tool to be used in the biological evaluation of UCHL1.

Carboxylate isosteres for caspase inhibitors: The acylsulfonamide case revisited

As part of an ongoing effort to discover inhibitors of caspase-1 with an optimized selectivity and biopharmaceutical profile, acylsulfonamides were explored as carboxylate isosteres for caspase inhibitors. Acylsulfonamide analogues of the clinically investigated caspase-1 inhibitor VRT-043198 and of the pan-caspase inhibitor Z-VAD-CHO were synthesized. The isostere-containing analogues with an aldehyde warhead had inhibitory potencies comparable to the carboxylate references. In addition, the conformational and tautomeric characteristics of these molecules were determined using 1H- and 13C-based NMR. The propensity of acylsulfonamides with an aldehyde warhead to occur in a ring-closed conformation at physiological pH significantly increases the sensitivity to hydrolysis of the acylsulfonamide moiety, yielding the parent carboxylate containing inhibitors. These results indicate that the acylsulfonamide analogues of the aldehyde-based inhibitor VRT-043198 might have potential as a novel type of prodrug for the latter. Finally, inhibition of caspase 1 and 11 mediated inflammation in mouse macrophages was found to correlate with the potencies of the compounds in enzymatic assays.

Soluble alpha-amino acid salts in acetonitrile: practical technology for the production of some dipeptides.

Alpha-amino acids are soluble in acetonitrile when treated with phosphazene bases. As a result, the protection/deprotection events that are usually required for peptide coupling reactions can be minimized. This is illustrated in the synthesis of the important angiotensin-converting enzyme (ACE) inhibitor enalapril. [reaction: see text]