139545-04-3

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid is used as a building block for the synthesis of pharmaceuticals and biologically active molecules. Its unique structure, including the phenyl group and the pentenoic acid group, allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid serves as a versatile intermediate for the preparation of various organic compounds. The presence of the Boc protecting group allows for selective deprotection and functionalization of the amino group, facilitating the synthesis of complex molecules with specific properties and functions.
Used in Research and Development:
(2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid is also utilized in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science. Its unique structural features make it an attractive candidate for studying new synthetic methodologies and reaction mechanisms.

Upstream product

• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 116246-06-1 (E)-(S)-4-tert-Butoxycarbonylamino-5-phenyl-pent-2-enoic acid ethyl ester 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 72155-45-4 Boc-L-phenylalaninal 
• 3095-95-2 diethylphosphonoacetic acid 
• 99298-05-2 (E)-(S)-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester 

Downstream Products

• 142723-72-6 (E)-(S)-4-((E)-(S)-4-tert-Butoxycarbonylamino-5-phenyl-pent-2-enoylamino)-5-phenyl-pent-2-enoic acid methyl ester 
• 637001-67-3 (S,E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpent-2-enoic acid 
• 195867-20-0 (4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpentanoic acid 
• 63328-06-3 (4R)-4-amino-5-phenylpentanoic acid 
• 269078-74-2 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid 
• 756485-04-8 MDL 28170 
• 760214-57-1 (E)-(S)-4-[3-(4-phenoxy-phenyl)-ureido]-5-phenyl-pent-2-enoic acid 
• 760214-65-1 (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid 
• 299182-18-6 tert-butyl (1S)-5-diazo-1-benzyl-4-oxopentylcarbamate 

Relevant academic research and scientific papers

Design of Gallinamide A Analogs as Potent Inhibitors of the Cysteine Proteases Human Cathepsin L and Trypanosoma cruzi Cruzain

Gallinamide A, originally isolated with a modest antimalarial activity, was subsequently reisolated and characterized as a potent, selective, and irreversible inhibitor of the human cysteine protease cathepsin L. Molecular docking identified potential modifications to improve binding, which were synthesized as a suite of analogs. Resultingly, this current study produced the most potent gallinamide analog yet tested against cathepsin L (10, Ki = 0.0937 ± 0.01 nM and kinact/Ki = 8 730 000). From a protein structure and substrate preference perspective, cruzain, an essential Trypanosoma cruzi cysteine protease, is highly homologous. Our investigations revealed that gallinamide and its analogs potently inhibit cruzain and are exquisitely toxic toward T. cruzi in the intracellular amastigote stage. The most active compound, 5, had an IC50 = 5.1 ± 1.4 nM, but was relatively inactive to both the epimastigote (insect stage) and the host cell, and thus represents a new candidate for the treatment of Chagas disease.

Structural features and molecular aggregations of designed triple-stranded β-sheets in single crystals

Design, synthesis and single-crystal conformations of hybrid triple-stranded β-sheets composed of E-vinylogous residues are reported. Restricting conformational flexibility of β-strands through the insertion of carbon-carbon double bonds at facing positio

HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: Synthesis and stereochemical analysis of β-benzotriazole N-oxide substituted γ-amino acids and hybrid peptides

HBTU is a standard coupling agent commonly used for the activation of free carboxylic acids during the solution and solid phase peptide synthesis. 1-Hydroxybenzotriazole (HOBt) plays a significant role in reducing the racemization during peptide synthesis

Self-assembly to function: Design, synthesis, and broad spectrum antimicrobial properties of short hybrid e -vinylogous lipopeptides

Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.

GLYT2 MODULATORS

α-, β-, and γ-amino acid derivatives of formula I are disclosed as selective GlyT2 inhibitors for the treatment of central nervous system (CNS) conditions such as muscle spasticity, tinnitus, epilepsy and neuropathic pain. Formula I

Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives

Several β- and γ-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [ 14C]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) were evaluated. A range of lipoph

Stereoselective synthesis of vinylogous peptides

A trans or cis ethenyl group has been inserted between the α-carbon and the carboxyl group of α-aminoacids by Horner stereoselective olefination of α-aminoaldehydes. Numerous pure cis and trans vinylogous α-aminoacids have been obtained thus and coupled w

Trifluoroacetic acid-mediated intramolecular formal N-H insertion reactions with amino-α-diazoketones: A facile and efficient synthesis of optically pure pyrrolidinones and piperidinones

Trifluoroacetic acid (TFA) was found to promote intramolecular formal N-H insertion reactions. Upon treatment with TFA, optically pure N-Boc-β′-amino-α-diazoketones (5a-c) and N-Boc-γ′-amino-α-diazoketones (10a-d) can be converted, with retention of chira

Use of ozonolysis in the synthesis of C-terminal peptide aldehydes on solid support

A new strategy for the synthesis of peptide aldehydes on solid support is presented. Reaction of a N-protected aminoaldehyde with caboethoxymethylene triphenylphosphorane yielded an α-β-unsaturated δ- amino derivative. After saponification, the resulting α-β-unsaturated δ- aminoacid was anchored to a solid support by an ester linkage (Merrifield resin) or by an amide linkage (MBHA, Expansin). After elongation of the peptide chain, ozonolysis yielded quite pure C-terminal peptide aldehydes in a good yield with no detectable racemization of the C-terminal residue.