16816-28-7

Basic information

• Product Name: methyl N-[(benzyloxy)carbonyl]glycylalaninate
• CAS NO: 16816-28-7
• Molecular Formula: C₁₄H₁₈N₂O₅
• Molecular Weight: 294.3031
• Mol File: 16816-28-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 495.4°C at 760 mmHg
• Flash Point: 253.4°C
• Density: 1.209g/cm³
• Vapor Pressure: 5.91E-10mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: methyl N-[(benzyloxy)carbonyl]glycylalaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-[(benzyloxy)carbonyl]glycylalaninate(16816-28-7)
• EPA Substance Registry System: methyl N-[(benzyloxy)carbonyl]glycylalaninate(16816-28-7)

Safety Data

• Hazardous Substances Data: 16816-28-7(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 133010-18-1 Z-glycine fluoride 
• 10073-22-0 ZGly, dicyclohexylammonium salt 
• 60341-62-0 carbobenzyloxyglycinesuccinimido ester 
• 96452-60-7 N-(Benzyloxycarbonyl)glycin-2-pyridylester 
• 67-56-1 methanol 
• 10065-72-2 L-Alanine methyl ester 
• 71785-38-1 Z-Gly-O-hexafluorisopropyl 
• 116287-43-5 N-thioacetyl-L-alanine methyl ester 

Downstream Products

• 23404-17-3 benzyloxycarbonylglycyl-alanine hydrazide 
• 121428-48-6 Gly-Ala-Val-OH 
• 97986-02-2 ({(S)-1-[(S)-1-(4-Nitro-phenylcarbamoyl)-ethylcarbamoyl]-ethylcarbamoyl}-methyl)-carbamic acid benzyl ester 
• 85589-15-7 3-carboxypropionylglycyl-alanyl-alanine p-nitroanilide 
• 3079-63-8 (S)-2-(2-Benzyloxycarbonylamino-acetylamino)-propionic acid 
• 122092-82-4 methyl 1-benzyloxycarbonyl-2-methyl-4-oxoimidazolidin-2-carboxylate 
• 122092-77-7 N-benzyloxycarbonylglycyl-α-methoxyalanine methyl ester 

Relevant articles and documents

Fluorous Coupling Reagents: Application of 2-Chloro-4,6- bis[(heptadecafluorononyl)oxy]-1,3,5-triazine in Peptide Synthesis

Benzyloxycarbonyl N-protected and C-terminus methyl ester protected amino acids react in THF in the presence of 4-methylmorpholine and fluorous condensation reagent, 2-chloro-4,6-bis[(heptadecafluorononyl)oxy[-1,3,5- triazine, to form di- and tripeptides

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.

Substrate-directed lewis-acid catalysis for peptide synthesis

A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: (1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; (2) the reaction proceeds without any racemization; (3) the new substrate-directed chemical ligation using the titanium catalyst is applicable to convergent peptide synthesis. These advantages overcome some of the unresolved problems in classical peptide synthesis.