198756-82-0

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzenemethanamine, α-methyl-2-nitro-, (αS)is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structure and reactivity. Its chiral nature allows for the development of enantiomerically pure compounds, which can exhibit different biological activities and improve the efficacy and safety of medications.
Used in Organic Chemistry:
Benzenemethanamine, α-methyl-2-nitro-, (αS)is also utilized in organic chemistry as a versatile building block for the synthesis of a wide range of organic compounds. Its reactivity and functional groups enable the formation of various chemical bonds and the creation of complex molecular structures, contributing to the advancement of organic synthesis and the development of new materials and compounds.
It is crucial to handle Benzenemethanamine, α-methyl-2-nitro-, (αS)with care, as it may possess hazardous properties. Proper safety precautions should be followed during its use to ensure the well-being of individuals and the environment.

Upstream product

• 2354-91-8 (S)-2,2,2-trifluoro-(α-methylbenzyl)acetamide 
• 577-59-3 2-acetylnitrobenzene 
• 3205-25-2 (R)-(-)-1-(2-nitrophenyl)-1-ethanol 

Downstream Products

• 1117218-57-1 N-((S)-1-(2-nitrophenyl)ethyl)acetamide 
• 1362627-19-7 C₂₂H₂₉N₃O₅ 

Relevant academic research and scientific papers

Modulation of RNA tertiary folding by incorporation of caged nucleotides

(Figure Presented) Knock it off: Individual RNA nucleotides with a caged nucleobase were incorporated, through their phosphoramidites, into a 160-mer RNA molecule that adopts a specific tertiary structure (see picture). Position-dependent local and global

Stereoelectronic effects in the reaction of aromatic substrates catalysed by: Halomonas elongata transaminase and its mutants

A transaminase from Halomonas elongata and four mutants generated by an in silico-based design were recombinantly produced in E. coli, purified and applied to the amination of mono-substituted aromatic carbonyl-derivatives. While benzaldehyde derivatives were excellent substrates, only NO2-acetophenones were transformed into the (S)-amine with a high enantioselectivity. The different behaviour of wild-type and mutated transaminases was assessed by in silico substrate binding mode studies.

Synthesis and Characterization of Nitroaromatic Peptoids: Fine Tuning Peptoid Secondary Structure through Monomer Position and Functionality

N-Substituted glycine oligomers, or peptoids, have emerged as an important class of foldamers for the study of biomolecular interactions and for potential use as therapeutic agents. However, the design of peptoids with well-defined conformations a priori remains a formidable challenge. New approaches are required to address this problem, and the systematic study of the role of individual monomer units in the global peptoid folding process represents one strategy. Here, we report our efforts toward this approach through the design, synthesis, and characterization of peptoids containing nitroaromatic monomer units. This work required the synthesis of a new chiral amine building block, (S)-1-(2-nitrophenyl)ethanamine (s2ne), which could be readily installed into peptoids using standard solid-phase peptoid synthesis techniques. We designed a series of peptoid nonamers that allowed us to probe the effects of this relatively electron-deficient and sterically encumbered a-chiral side chain on peptoid structure, namely, the peptoid threaded loop and helix. Circular dichroism spectroscopy of the peptoids revealed that the nitroaromatic monomer has a significant effect on peptoid secondary structure. Specifically, the threaded loop structure was disrupted in a nonamer containing alternating V-(S)-1-phenylethylglycine (VVspe) and VVs2ne monomers, and the major conformation was helical instead. Indeed, placement of a single Ns2ne at the N-terminal position of (VVspe)9 resulted in a destabilized form of the threaded loop structure relative to the homononamer (VVspe)9. Conversely, we observed that incorporation of V-(S)-1-(4-nitrophenyl)ethylglycine (VVsnp, a p-nitro monomer) at the VV-terminal position stabilized the threaded loop structure relative to (VVspe)9. Additional experiments revealed that nitroaromatic side chains can influence peptoid nonamer folding by modulating the strength of key intramolecular hydrogen bonds in the peptoid threaded loop structure. Steric interactions were also implicated for the VVs2ne monomer. Overall, this study provides further evidence that aromatic side-chain structure, even if perturbed in a single monomer unit, can strongly influence local peptoid backbone conformation.