197517-41-2

Upstream product

• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 63-91-2 L-phenylalanine 
• 1072896-51-5 2,5-dioxopyrrolidin-1-yl 5-chloro-2-hydroxybenzoate 
• 1734-62-9 2-acetoxy-5-chloro-benzoic acid 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 63-91-2 L-phenylalanine 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 

Relevant academic research and scientific papers

Ochratoxin A acts as a photoactivatable DNA cleaving agent

The ability of ochratoxin A to photoinduce DNA cleavage is described; in the presence of DNA the photoreaction yields the non-chlorinated derivative, ochratoxin B, while a hydroquinone derivative is produced under anaerobic conditions.

Multi-Institution Research and Education Collaboration Identifies New Antimicrobial Compounds

New antibiotics are urgently needed to address increasing rates of multidrug resistant infections. Seventy-six diversely functionalized compounds, comprising five structural scaffolds, were synthesized and tested for their ability to inhibit microbial growth. Twenty-six compounds showed activity in the primary phenotypic screen at the Community for Open Antimicrobial Drug Discovery (CO-ADD). Follow-up testing of active molecules confirmed that two unnatural dipeptides inhibit the growth of Cryptococcus neoformans with a minimum inhibitory concentration (MIC) ≤ 8 μg/mL. Syntheses were carried out by undergraduate students at five schools implementing Distributed Drug Discovery (D3) programs. This report showcases that a collaborative research and educational process is a powerful approach to discover new molecules inhibiting microbial growth. Educational gains for students engaged in this project are highlighted in parallel to the research advances. Aspects of D3 that contribute to its success, including an emphasis on reproducibility of procedures, are discussed to underscore the power of this approach to solve important research problems and to inform other coupled chemical biology research and teaching endeavors.

Effect of the mimic structure on the molecular recognition properties of molecularly imprinted polymers for ochratoxin A prepared by a fragmental approach

In this work the fragmental approach was used to prepare several molecularly imprinted ethylene dimethacrylate-co-methacrylic acid polymers with molecular recognition towards the mycotoxin ochratoxin A, with the aim of searching for simpler mimic template

A kinetic study into the hydrolysis of the ochratoxins and analogues by carboxypeptidase A

The hydrolyses of the ochratoxins and analogues by carboxypeptidase A were assessed. This was done by measuring the amount of phenylalanine formed with liquid chromatography coupled to tandem electrospray mass spectrometry. The kinetic data of ochratoxin A, ochratoxin B, and the synthetic bromo-ochratoxin B were compared to the values of a number of synthesized structure analogues, namely, ochratoxin A methyl ester, ochratoxin B methyl ester, N-(2-hydroxybenzoyl)phenylalanine, N-(5-chloro-2-hydroxybenzoyl)phenylalanine, N-(5-bromo-2-hydroxybenzoyl)phenylalanine, and N-(5-fluoro-2-hydroxybenzoyl)phenylalanine. The halogen-containing analogues had lower turnovers than their des-halo analogues. There are no substantial differences in the kinetic data between the different halogen-containing analogues.

The synthesis of bromo- and iodo-ochratoxin B

The effective synthesis of bromo- and iodo-ochratoxin B by the treatment of ochratoxin B with pyridinium hydrobromide perbromide, and iodine and mercury(II)oxide, respectively, is reported.

On the role of copper and iron in DNA cleavage by ochratoxin A. Structure-activity relationships in metal binding and copper-mediated DNA cleavage

Ochratoxin A (OTA, 1: X = Cl) is a fungal carcinogen that facilitates single-strand DNA cleavage and DNA adduction when metabolically activated. To determine if redox-active transition metals induce OTA-mediated DNA damage, we have examined the toxin's ab