185540-61-8

Basic information

• Product Name: Benzoic acid, 3-(2-bromoethoxy)-4-nitro-, methyl ester
• CAS NO: 185540-61-8
• Molecular Formula: C10H10BrNO5
• Molecular Weight: 304.097
• Mol File: 185540-61-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-(2-bromoethoxy)-4-nitro-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-(2-bromoethoxy)-4-nitro-, methyl ester(185540-61-8)
• EPA Substance Registry System: Benzoic acid, 3-(2-bromoethoxy)-4-nitro-, methyl ester(185540-61-8)

Safety Data

• Hazardous Substances Data: 185540-61-8(Hazardous Substances Data)

Upstream product

• 713-52-0 methyl 3-hydroxy-4-nitrobenzoate 
• 540-51-2 2-bromoethanol 
• 106-93-4 ethylene dibromide 

Downstream Products

• 185540-69-6 (S)-2-{[4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-7-carbonyl]-amino}-pentanedioic acid diethyl ester 
• 185540-68-5 (S)-2-{[4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-7-carbonyl]-amino}-hexanedioic acid dimethyl ester 
• 185540-65-2 3-(2-Bromo-ethoxy)-4-(toluene-4-sulfonylamino)-benzoic acid methyl ester 
• 185540-66-3 4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-7-carboxylic acid methyl ester 
• 185540-67-4 4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-7-carboxylic acid 
• 1026967-05-4 4-(Toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-7-carbonyl chloride 
• 185540-64-1 4-Amino-3-(2-bromo-ethoxy)-benzoic acid methyl ester 

Relevant articles and documents

Mechanistic Studies on CysS - A Vitamin B12-Dependent Radical SAM Methyltransferase Involved in the Biosynthesis of the tert-Butyl Group of Cystobactamid

Cobalamin (Cbl)-dependent radical S-adenosylmethionine (SAM) methyltransferases catalyze methylation reactions at non-nucleophilic centers in a wide range of substrates. CysS is a Cbl-dependent radical SAM methyltransferase involved in cystobactamid biosynthesis. This enzyme catalyzes the sequential methylation of a methoxy group to form ethoxy, i-propoxy, s-butoxy, and t-butoxy groups on a p-aminobenzoate peptidyl carrier protein thioester intermediate. This biosynthetic strategy enables the host myxobacterium to biosynthesize a combinatorial antibiotic library of 25 cystobactamid analogues. In this Article, we describe three experiments to elucidate how CysS uses Cbl, SAM, and a [4Fe-4S] cluster to catalyze iterative methylation reactions: a cyclopropylcarbinyl rearrangement was used to trap the substrate radical and to estimate the rate of the radical substitution reaction involved in the methyl transfer; a bromoethoxy analogue was used to explore the active site topography; and deuterium isotope effects on the hydrogen atom abstraction by the adenosyl radical were used to investigate the kinetic significance of the hydrogen atom abstraction. On the basis of these experiments, a revised mechanism for CysS is proposed.