22221-83-6

Basic information

• Product Name: methyl ((benzyloxy)carbonyl)-D-valyl-L-alaninate
• Synonyms: methyl ((benzyloxy)carbonyl)-D-valyl-L-alaninate
• CAS NO: 22221-83-6
• Molecular Weight: 336.388
• Mol File: 22221-83-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl ((benzyloxy)carbonyl)-D-valyl-L-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl ((benzyloxy)carbonyl)-D-valyl-L-alaninate(22221-83-6)
• EPA Substance Registry System: methyl ((benzyloxy)carbonyl)-D-valyl-L-alaninate(22221-83-6)

Safety Data

• Hazardous Substances Data: 22221-83-6(Hazardous Substances Data)

Upstream product

• 10065-72-2 L-Alanine methyl ester 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 72-18-4 L-valine 
• 501-53-1 benzyl chloroformate 
• 67-56-1 methanol 
• 93936-31-3 Cbz-Val-Ala-NH₂ 
• 133010-20-5 Cbz-Val-F 
• 54647-77-7 N-[(benzyloxy)carbonyl]-L-valine, compound with dicyclohexylamine (1:1) 
• 1685-33-2 N-[(benzyloxy)carbonyl]-D-valine 

Downstream Products

• 80165-13-5 {(S)-1-[(S)-1-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester 
• 17445-33-9 (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)propanoic acid 
• 16816-23-2 N-(benzyloxycarbonyl)-L-leucyl-L-valcyl-L-alanine methyl ester 
• 1361509-39-8 (S)-methyl 2-((S)-2-(benzyloxycarbonylamino)-3-methylbutaneselenoamido)propanoate 
• 77834-27-6 Z-Ile-Ile-Val-Ala-NHNH₂ 
• 77834-26-5 Z-Ile-Ile-Val-Ala-OMe 
• 77834-25-4 Z-Ile-Val-Ala-OMe 

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.

Synthesis of selenoxo peptides and oligoselenoxo peptides employing LiAlHSeH

Synthesis of selenoxo peptides by the treatment of Nα- protected peptide esters with a combination of PCl5 and LiAlHSeH is delineated. The method is simple, high-yielding, and free from racemization. Thus obtained selenoxo peptides are used as units for N-terminal chain extension through Nα-deprotection/coupling to yield peptide-selenoxo peptide hybrids. Multiple selenation is demonstrated by conversion of two peptide bonds of tripeptides into selenoxo peptide bonds. Amino acid derived arylamides are also converted into aryl selenoamides. C6H 5-CSeNH-Val-OMe 8f is obtained as single crystal, and its structure was determined through X-ray diffraction study.

Ethyl propiolate: A simple and convenient peptide coupling reagent

Ethyl propiolate has been used to activate N-protected amino acids to form a moderately activated vinyl-ester which aminolysis requires a catalytic amount of sodium bisulfite.