400653-36-3

Basic information

• Product Name: 1-BOC-BENZIMIDAZOLE-5-CARBOXILIC ACID
• Synonyms: 1-BOC-BENZIMIDAZOLE-5-CARBOXILIC ACID
• CAS NO: 400653-36-3
• Molecular Formula: C₁₃H₁₄N₂O₄
• Molecular Weight: 262.264
• Mol File: 400653-36-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BOC-BENZIMIDAZOLE-5-CARBOXILIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-BENZIMIDAZOLE-5-CARBOXILIC ACID(400653-36-3)
• EPA Substance Registry System: 1-BOC-BENZIMIDAZOLE-5-CARBOXILIC ACID(400653-36-3)

Safety Data

• Hazardous Substances Data: 400653-36-3(Hazardous Substances Data)

Usage

Structure

A derivative of benzimidazole, which is a heterocyclic compound containing a fused benzene and imidazole ring.

Functional groups

Contains a BOC (tert-butyloxycarbonyl) group, a protecting group used in organic synthesis to protect amines and other reactive functional groups from unwanted reactions.

Applications

Potential applications in pharmaceuticals, drug development, and organic synthesis as a building block for synthesizing complex molecules.

Importance

Crucial for the development of new drugs and novel chemicals due to its unique structure and reactivity.

Reactivity

The BOC group can be removed under acidic conditions, allowing for further functionalization and modification of the molecule.

Solubility

Generally soluble in organic solvents such as dimethyl sulfoxide (DMSO), methanol, and ethanol.

Stability

Stable under normal laboratory conditions, but sensitive to strong acids and bases that can remove the BOC protecting group.

Purity

Typically available with a high level of purity, which is essential for its use in pharmaceutical and chemical research.

Safety

As with any chemical compound, it is essential to handle 1-BOC-BENZIMIDAZOLE-5-CARBOXILIC ACID with care, following proper safety protocols and guidelines to minimize potential hazards.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 15788-16-6 5-benzimidazolecarboxylic acid 

Downstream Products

• 400653-37-4 1-Cbz-3-[[1-(t-butyloxycarbonyl)benzimidazol-5-yl]-carbonyl]aminopyrrolidine 
• 1098591-74-2 C₁₆H₁₅ClN₃O₄P 
• 401791-61-5 (S)-5-(1-tert-butoxycarbonyl-3-phenyl-propylcarbamoyl)-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 401791-59-1 5-[(tert-butoxycarbonyl-phenyl-methyl)-carbamoyl]-benzoimidazole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

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New dsDNA binding unnatural oligopeptides with pyrimidine selectivity

Solid phase peptide library screening followed by extension of a lead recognition element for binding to a dsDNA sequence (NF binding site of IL6) using solution phase screening, delivered a new DNA binding peptide, Ac-Arg-Ual-Sar-Chi-Chi-Tal-Arg-CONH2. In the present research, the contribution of the different amino acid side chains to the binding strength of the peptide to dsDNA was investigated using an ethidium bromide displacement test. Based on these results, the lead structure was optimized by deconvolution. Eight new unnatural amino acids were evaluated at two positions of the heptapeptide replacing the Ual-Sar fragment. The strongest dsDNA binding was observed using {[(3-chlorophenyl)methyl]amino}acetic acid (Cbg) and β-cyclohexyl-l-alanine (Cha) respectively, at those two positions. A 10-fold increase in affinity compared to the Ual-Sar sequence was obtained. Further enhancement of dsDNA binding was obtained with hybrid molecules linking the newly developed peptide fragment to an acridine derivative with a flexible spacer. This resulted in ligands with affinities in the μM range for the dsDNA target (Kd of 2.1×10-6 M). DNase I footprinting with the newly developed oligopeptide motifs showed the presence of a pronounced pyrimidine specificity, while conjugation to an intercalator seems to redirect the interaction to mixed sequences. This way, new unnatural oligopeptide motifs and hybrid molecules have been developed endowed with different sequence selectivities. The results demonstrate that the unnatural peptide library approach combined with subsequent modification of selected amino acid positions, is very suited for the discovery of novel sequence-specific dsDNA binding ligands.