61128-08-3

Usage

InChI:InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)/i1+1,2+1

Upstream product

• 33458-49-0 <1,2-(13)C2>dibromoethane 
• 151-50-8 potassium cyanide 
• 83587-79-5 <2,3-¹³C₂>-succinonitrile 
• 101391-58-6 [2,3-¹³C₂]acetylenedicarboxylic acid 
• 79341-52-9 1,2-Diphenyl-<1,2-13C2>ethan 

Relevant academic research and scientific papers

Antibiotics from Gliding Bacteria, XLI. - On the constitution of Myxovirescins B-T and Biogenesis of Myxovirescin A.

The gliding bacteria Myxococcus virescens Mx v48 produce the myxovirescins A-T, macrocyclic lactam-lactones which differ in ring size, oxidation levels of C-121, C-20, and C-24, alkylation at C-16, and in the presence of a double bond at C26-C27.Incorporation experiments using 2>succinic acid as well as diethyl malonate indicate that the 16-ethyl group in myxovirescin A originates from the succinate/methyl malonate path.

Biosynthesis of the Macrotetrolide Antibiotics; The Incorporation of Carbon-13 and Oxygen-18 Labelled Acetate, Propionate, and Succinate

The biosynthesis of the macrotetrolide antibiotics, in particular nonactin, has been studied using carbon-13 and oxygen-18 enriched acetate and propionate, as well as carbon-13 enriched succinate, in feeding experiments with the producing organism Streptomyces griseus.A protocol is described which allows the separation of derivatives formed from each enantiomer of nonactic and homononactic acids.From a study of the incorporation of the labelled precursors into these derivatives it could be shown that the origins of the carbon and oxygen atoms in each enantiomer are identical.The carbon backbone of nonactic acid is assembled from two acetate, one succinate, and one propionate units, and the C-O bonds at C-8, C-6, and C-1 are derived intact from the primary precursors.Based on these data a new proposal is made to account for the biosynthesis of (+/-)-nonactate, and nonactin, in S. griseus.

Degenerate Carbon Skeleton Isomerization of the Cyclopentyl Cation in the Gas Phase. Experimental and Theoretical Evidence for the Existence of a Pyramidal C5H9(+) Cation as an Intermediate in the Unimolecular Ethylene Elimination

The investigation of 13C2-labelled isotopomeric bromocyclopentanes (5a, b), cyclobutylmethyl bromide (6a) and 5-bromo-1-pentenes (7a, b) clearly demonstrates, that unimolecular ethylene loss from the gaseous + ions generated from both the cyclic and acyclic precursors is preceded by complete carbon scrambling.Whereas the degenerate isomerization 8a 8b can, in principle, proceed either via the bisected cyclobutylmethyl cation 9 or via the non-classical, pyramidal cation 3, the MINDO/3 calculations reveal, that ethylene loss from C5H9+ involves 3 as an intermediate.From 3 a transition state is reached which can be regarded as a partially opened cyclopropyl cation "solvated" by interaction with C2H4.Descriptions of the syntheses of the 13C2-labelled bromides are given.