1198-67-0

Usage

Molecular class

Pyrrole carboxylic acid derivative

Structure

Methyl ester derivative of 3,4,5-tribromo-1H-pyrrole-2-carboxylic acid

Usage

Organic synthesis and pharmaceutical research

Biological activities

Potential biological activities

Intermediate

Used as an intermediate in the production of various pharmaceuticals and agrochemicals

Handling precautions

Potential hazards and risks associated with its handling and use.

Upstream product

• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 

Downstream Products

• 86288-60-0 3,4,5-Tribromo-1-[2-(4-methylsulfanyl-phenyl)-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester 
• 86288-61-1 3,4,5-Tribromo-1-{2-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-phenyl]-ethyl}-1H-pyrrole-2-carboxylic acid methyl ester 
• 86288-58-6 3,4,5-Tribromo-1-phenethyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 86289-13-6 3,4,5-Tribromo-1-(2-oxo-2-phenyl-ethyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 1016650-05-7 methyl 5-(4-tert-butylphenyl)-3,4-dibromo-1H-pyrrole-2-carboxylate 
• 62541-32-6 3,4,5-Tribromo-1-phenethyl-1H-pyrrole-2-carboxylic acid 
• 86288-64-4 3,4,5-Tribromo-1-{2-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-phenyl]-ethyl}-1H-pyrrole-2-carboxylic acid 
• 86288-72-4 3,4,5-Tribromo-1-{2-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-phenyl]-ethyl}-1H-pyrrole-2-carbonyl chloride 
• 86288-71-3 3,4,5-Tribromo-1-[2-(4-methylsulfanyl-phenyl)-ethyl]-1H-pyrrole-2-carbonyl chloride 
• 86288-63-3 3,4,5-Tribromo-1-[2-(4-methylsulfanyl-phenyl)-ethyl]-1H-pyrrole-2-carboxylic acid 
• 86288-69-9 3,4,5-Tribromo-1-phenethyl-1H-pyrrole-2-carbonyl chloride 
• 86289-00-1 6,7,8-Tribromo-3-phenyl-3,4-dihydro-pyrrolo[2,1-c][1,4]oxazin-1-one 
• 74039-30-8 3,4,5-tribromo-1H-pyrrole-2-carboxylic acid 

Relevant academic research and scientific papers

Gatekeeping Ketosynthases Dictate Initiation of Assembly Line Biosynthesis of Pyrrolic Polyketides

Assembly line biosynthesis of polyketide natural products involves checkpoints where identities of thiotemplated intermediates are verified before polyketide extension reactions are allowed to proceed. Determining what these checkpoints are and how they operate is critical for reprogramming polyketide assembly lines. Here we demonstrate that ketosynthase (KS) domains can perform this gatekeeping role. By comparing the substrate specificities for polyketide synthases that extend pyrrolyl and halogenated pyrrolyl substrates, we find that KS domains that need to differentiate between these two substrates exercise high selectivity. We additionally find that amino acid residues in the KS active site facilitate this selectivity and that these residues are amenable to rational engineering. On the other hand, KS domains that do not need to make selectivity decisions in their native physiological context are substrate-promiscuous. We also provide evidence that delivery of substrates to polyketide synthases by non-native carrier proteins is accompanied by reduced biosynthetic efficiency.

Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations

Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 °C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 μmol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4- ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2- carboxamide (from Acanthella carteri).