35150-09-5

Basic information

• Product Name: BOC-GLY-NH2
• Synonyms: BOC-GLY-NH2;TERT-BUTYL CARBAMOYLMETHYLCARBAMATE;TERT-BUTYL 2-AMINO-2-OXOETHYLCARBAMATE;Boc-Glycinamide;N-tert-Butoxycarbonyl-L-glycinamide;N-Boc-glycinaMide, 95%;tert-butyl N-(2-amino-2-oxoethyl)carbamate;(Tert-Butoxy)Carbonyl Gly-NH2
• CAS NO: 35150-09-5
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• EINECS: 1533716-785-6
• Mol File: 35150-09-5.mol

Chemical Properties

• Melting Point: 85-87 °C
• Boiling Point: 339.677 °C at 760 mmHg
• Flash Point: 159.2 °C
• Appearance: White/Solid
• Density: 1.108 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 12.01±0.46(Predicted)
• CAS DataBase Reference: BOC-GLY-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-GLY-NH2(35150-09-5)
• EPA Substance Registry System: BOC-GLY-NH2(35150-09-5)

Safety Data

• Hazardous Substances Data: 35150-09-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-GLY-NH2 is used as a synthetic intermediate for the preparation of primary amides, which act as selective inhibitors of cathepsin K. Cathepsin K is a protease enzyme implicated in bone resorption, and its inhibition can be beneficial in treating conditions like osteoporosis and rheumatoid arthritis.
Used in Vaccine Development:
In the field of vaccine development, BOC-GLY-NH2 is utilized in the preparation of group A streptococcal vaccines. Group A streptococcus is a bacterium responsible for various infections, including strep throat and flesh-eating disease. The development of a vaccine using BOC-GLY-NH2 can potentially help in preventing these infections and reducing their associated morbidity and mortality.

InChI:InChI=1/C7H14N2O3/c1-7(2,3)12-6(11)9-4-5(8)10/h4H2,1-3H3,(H2,8,10)(H,9,11)

Upstream product

• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 
• 50903-47-4 perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate 
• 3655-05-8 tert-butoxycarbonylglycine p-nitrophenylester 

Downstream Products

• 85363-04-8 tert-butyl cyanomethylcarbamate 
• 182120-87-2 2-tert-butoxycarbonylaminoacetimidic acid ethyl ester 
• 73017-97-7 N-<(tert-butoxycarbonyl)amino>methylamine 
• 848086-43-1 [1-[(tert-butoxycarbonylamino-methyl)-carbamoyl]-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 71904-80-8 2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid 
• 186453-48-5 2-((S)-1-{[2-((R)-1-{[2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carbonyl]-amino}-ethyl)-5-methyl-oxazole-4-carboxylic acid pentafluorophenyl ester 
• 182120-90-7 2-({[(tert-butoxy)carbonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid 
• 182120-97-4 tert-butyl((4-carbamoyloxazol-2-yl)methyl)carbamate 
• 182120-89-4 methyl 2-({[(tert-butoxy)carbonyl]amino}methyl)-1,3-oxazole-4-carboxylate 
• 1312951-16-8 C₃₃H₄₀N₄O₄ 
• 1312951-15-7 C₃₃H₄₀N₄O₄ 
• 27904-92-3 N-glycyl>aniline 
• 1387683-52-4 C₁₃H₁₇ClN₂O₃ 
• 1387759-21-8 C₁₄H₂₀N₂O₃ 

Relevant articles and documents

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.

Parallel synthesis of an oligomeric imidazole-4, 5-dicarboxamide library

A library of oligomeric compounds was synthesized based on the imidazole-4, 5-dicarboxylic acid scaffold along with amino acid esters and chiral diamines derived from amino acids. The final compounds incorporate nonpolar amino acids (Leu, Phe, Trp), polar amino acids (Ser, Asp, Arg), and neutral amino acids (Gly, Ala), and were designed to be useful in screening for inhibitors of protein-protein interactions. Many of the protected and deprotected oligomers show evidence of conformational isomers persistent at room temperature in aqueous solution. A total of 317 final oligomers, out of 441 targeted compounds, were obtained in high analytical purity and of sufficient quantity to submit them for high-throughput screening as part of the NIH Roadmap.