59897-41-5Relevant academic research and scientific papers
ISOLATION OF DIHYDROCLAVAMINIC ACID, AN INTERMEDIATE IN THE BIOSYNTHESIS OF CLAVULANIC ACID
Baldwin, Jack E.,Adlington, Robert M.,Bryans, Justin S.,Bringhen, Alain O.,Coates, Janice B.,et al.
, p. 4089 - 4100 (2007/10/02)
A primary isotope effect was utilised in an in vitro study to allow the isolation and characterisation of an intermediate between proclavaminic acid and clavaminic acid, in clavulanic acid biosynthesis.
Isolation of an Intermediate in Clavulanic Acid Biosynthesis
Baldwin, Jack E.,Adlington, Robert M.,Bryans, Justin S.,Bringhen, Alain O.,Coates, Janice B.,et al.
, p. 617 - 619 (2007/10/02)
The operation of a primary isotope effect was utilised to enable a hitherto unknown intermediate in clavulanic acid biosynthesis to be isolated and characterised.
Clavulanic Acid and its Derivatives. Structure Elucidation of Clavulanic Acid and the Preparation of Dihydroclavulanic Acid, Isoclavulanic acid, Esters and Related Oxidation Products
Brown, Allan G.,Corbett, David F.,Goodacre, Jennifer,Harbridge, John B.,Howarth, T. Trefor,et al.
, p. 635 - 650 (2007/10/02)
Clavulanic acid, a novel β-lactamase inhibitor from Streptomyces clavuligerus, has been shown to be Z-(2R,5R)-3-(β-hydroxyethylidene)-7-oxo-4-oxa-1-azabicycloheptane-2-carboxylic acid (1).The structure and absolute stereochemistry was confirmed by X-ray analysis of the p-nitrobenzyl and p-bromobenzyl esters, (14) and (15).The conversion of clavulanic acid into a variety of esters and acyl derivatives is described.An account of its isomerisation to the E isomer (30) and the formation of an oxetane (45) as a by-product of the photolysis of the phenacyl ester (18) is given.The reduction and oxidation of acid (1) under a variety of conditions has also been examined in detail.
