128293-64-1

Basic information

• Product Name: 4-TERT-BUTOXYCARBONYLAMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID
• Synonyms: 4-TERT-BUTOXYCARBONYLAMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID;4-tert-Butoxycarbonylamino-1-methyl-1H-imidazole;1H-Imidazole-2-carboxylicacid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-1-methyl-;4-(Boc-amino)-1-methyl-1H-imidazole-2-carboxylic acid≥ 98% (HPLC);BOC-NH(4)-MEIMD-(2)-OH;4-(BOC-AMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID;4-[(T-BUTOXYCARBONYL)AMINO]-1-METHYLIMIDAZOLE-2-CARBOXYLIC ACID;4-(Boc-amino)-1-methyl-1H-imidazole-2-carboxylic acid, 95%, freeze-dried powder
• CAS NO: 128293-64-1
• Molecular Formula: C₁₀H₁₅N₃O₄
• Molecular Weight: 241.24
• Mol File: 128293-64-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 200-201 °C
• Appearance: /
• Density: 1.29g/cm³
• Refractive Index: 1.558
• Storage Temp.: -15°C
• PKA: 1.22±0.32(Predicted)
• CAS DataBase Reference: 4-TERT-BUTOXYCARBONYLAMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTOXYCARBONYLAMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID(128293-64-1)
• EPA Substance Registry System: 4-TERT-BUTOXYCARBONYLAMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID(128293-64-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/37/38
• Safety Statements: 36/37-36/37/39-28-3
• Hazardous Substances Data: 128293-64-1(Hazardous Substances Data)

Usage

Chemical Properties

White to greyish white solid

Uses

4-(Boc-amino)-1-methyl-1H-imidazole-2-carboxylic Acid is used in the synthesis of polyamides containing imidazole and pyrrole amino acids. It is also used to prepare distamycin A analogs as DNA binding agents.

InChI:InChI=1/C10H15N3O4/c1-10(2,3)17-9(16)12-6-5-13(4)7(11-6)8(14)15/h5H,1-4H3,(H,12,16)(H,14,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 162085-97-4 methyl 4-amino-1-methyl-1H-imidazole-2-carboxylate 
• 128293-62-9 ethyl 4-amino-1-methylimidazole-2-carboxylate 
• 109012-23-9 ethyl 1-methyl-4-nitroimidazole-2-carboxylate 
• 18595-34-1 tert-butyl fluoroformate 
• 30148-23-3 2-trichloroacetyl-1-methylimidazole 
• 120095-64-9 2,2,2-trichloro-1-(1-methyl-4-nitro-1H-imidazol-2-yl)ethan-1-one 
• 169770-25-6 1-methyl-4-nitro-1H-imidazole-2-carboxylic acid methyl ester 
• 500701-36-0 methyl 4-[(tert-butoxycarbonyl)amino]-N-methyl-1H-imidazole-2-carboxylate 
• 128293-63-0 ethyl 4-tert-butyloxycarbonylamino-1-methylimidazole-2-carboxylate 

Downstream Products

• 252206-28-3 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid 

Relevant articles and documents

4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides

DNA-binding polyamides are synthetic oligomers of pyrrole/imidazole units with high specificity and affinity for double-stranded DNA. To increase their synthetic diversity, we report a mild methodology based on 4-methyltrityl (Mtt) solid phase peptide synthesis (SPPS), whose building blocks are more accessible than the standard Fmoc and Boc SPPS ones. We demonstrate the robustness of the approach by preparing and studying a hairpin with all precursors. Importantly, our strategy is orthogonal and compatible with sensitive molecules and could be readily automated.

SEQUENCE SELECTIVE PYRROLE AND IMIDAZOLE POLYAMIDE METALLOCOMPLEXES

The present invention relates to sequence selective compounds for targeting therapeutic or diagnostic groups to polynucleotides. More particularly, the present invention relates to sequence selective targeting of metallocomplexes, such as metallodrugs and metallodiagnostics, to polynucleotides.

Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids

Matrix presented Polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids are synthetic ligands that have an affinity and specificity for DNA comparable to those of many naturally occurring DNA binding proteins. A machine-assisted Fmoc solid phase synthesis of polyamides has been optimized to afford high stepwise coupling yields (>99%). Two monomer building blocks, Fmoc-Py acid and Fmoc-Im acid, were prepared in multigram scale. Cleavage by aminolysis followed by HPLC purification affords up to 200 mg quantities of polyamide with purities and yields greater than or equal to those reported using Boc chemistry. A broader set of reaction conditions will increase the number and complexity of minor groove binding polyamides which may be prepared and help ensure compatibility with many commercially available peptide synthesizers.