144-16-1

Usage

Uses

Used in Pharmaceutical Industry:
5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid) is used as a reagent for the synthesis of vibrioferrin, a siderophore. Siderophores are compounds that have a high affinity for iron and are used by bacteria to acquire this essential nutrient. The synthesis of vibrioferrin can be crucial in understanding bacterial iron uptake mechanisms and potentially developing new antimicrobial strategies.
Additionally, 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid) serves as a building block for the creation of lipophilic isosteres of nucleoside triphosphates (NTPs). These isosteres are potential inhibitors of HIV reverse transcriptase, an enzyme that plays a critical role in the replication of the HIV virus. By inhibiting this enzyme, the replication of the virus can be halted, offering a potential therapeutic approach to combat HIV infection.

InChI:InChI=1/C7H8O7/c8-4(9)1-7(2-5(10)11)6(12)13-3-14-7/h1-3H2,(H,8,9)(H,10,11)

Upstream product

• 50-00-0 formaldehyd 
• 77-92-9 citric acid 
• 15454-33-8 chloromethanol 
• 625-56-9 Chloromethyl acetate 
• 628-51-3 diacetoxymethane 
• 20757-83-9 [1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide 
• 17140-33-9 2-acetoxy-propane-1,2,3-tricarboxylic acid 

Downstream Products

• 77862-72-7 (5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid dimethyl ester 
• 83966-24-9 2-Hydroxy-1,2,3-propanetricarboxylic Acid 2-Isopropyl Ester 
• 83948-68-9 2-Hydroxy-1,2,3-propanetricarboxylic Acid 2-Benzyl Ester 
• 108872-07-7 [4-(benzylcarbamoyl-methyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid 
• 108872-58-8 {4-[(methyl-phenyl-carbamoyl)-methyl]-5-oxo-[1,3]dioxolan-4-yl}-acetic acid 
• 83948-79-2 Sodium; 3-[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-2-{[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-propionate 
• 83948-78-1 Sodium; 3-[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-2-{[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-propionate 
• 83948-75-8 Tribenzylarthrobactin 
• 83948-71-4 N-[3-(Acetyl-benzyloxy-amino)-propyl]-2-{[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinamic acid benzyl ester 
• 83948-74-7 2-{[3-(Acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinic acid 1-benzyl ester 4-(4-nitro-phenyl) ester 
• 83948-73-6 N-[3-(Acetyl-benzyloxy-amino)-propyl]-2-{[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinamic acid isopropyl ester 
• 83948-69-0 3-Benzyloxycarbonyl-3-hydroxy-pentanedioic acid bis-(4-nitro-phenyl) ester 
• 83966-25-0 2-isopropyl citrate 
• 39007-57-3 Arthrobactin 

Relevant academic research and scientific papers

An improved synthesis of trisodium (U)-homocitrate from citric acid

A method of synthesis of trisodium (R)-homocitrate starting from citric acid is reported. The procedure affords the final product of high optical purity with satisfactory yield.

Total synthesis of the siderophore vibrioferrin

Total synthesis of vibrioferrin (1), a siderophore, was achieved via chiral dibenzyl citrate separated by optical resolution. It was elucidated that the configuration of the citrate moiety of vibrio-ferrin was R.

Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

Resolution of a citric acid derivative: Synthesis of (R)-(-)-homocitric acid-γ-lactone

Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in ≤90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-α-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)- homocitric acid utilising an Amdt-Eistert homologation followed by acid eatalysed deprotection.

The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase

We describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophile derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5'-amino-d4T is included. Intramolecular rearrangement of several amide-linked isosteres are also reported, along with an alternative synthetic strategy to the desired amide-linked isosteres.

Isosteres of nucleoside triphosphates

This paper describes the design and synthesis of lipophilic isosteres of nucleoside triphosphates as potential inhibitors of HIV reverse transcriptase. The isosteric replacement of the triphosphate group is a modification of the citrate group.