5716-14-3Relevant academic research and scientific papers
The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: Improved practicality and broader scope
Ma, Paul,Kanizaj, Nicholas,Chan, Shu-Ann,Ollis, David L.,McLeod, Malcolm D.
supporting information, p. 6208 - 6214 (2014/08/05)
A library of steroid glucuronides was prepared using the glucuronylsynthase derived from Escherichia coli β-glucuronidase, followed by purification using solid-phase extraction. A representative range of steroid substrates were screened for synthesis on t
Experimental and kinetic studies of the Escherichia coli glucuronylsynthase: An engineered enzyme for the synthesis of glucuronide conjugates
Wilkinson, Shane M.,Watson, Morgan A.,Willis, Anthony C.,McLeod, Malcolm D.
scheme or table, p. 1992 - 2000 (2011/06/19)
The detection and study of glucuronide metabolites is essential in many fields including pharmaceutical development, sports drug testing, and the detection of agricultural residues. Therefore, the development of improved methods for the synthesis of glucuronide conjugates is an important aim. The glycosynthase derived from E. coli β-glucuronidase provides an efficient, scalable, single-step synthesis of β-glucuronides under mild conditions. In this article we report on experimental and kinetic studies of the E. coli glucuronylsynthase, including the influence of acceptor substrate, pH, temperature, cosolvents, and detergents, leading to optimized conditions for glucuronide synthesis. Enzyme kinetics also reveals that both substrate and product inhibition may occur in glucuronylsynthase reactions but that these effects can be ameliorated through the judicious choice of acceptor and donor substrate concentrations. An investigation of temporary polar substituents was conducted leading to improved aqueous solubility of hydrophobic steroidal acceptors. In this way the synthesis of the steroidal metabolite dehydroepiandrosterone 3-β-d-glucuronide was achieved in three steps and 86% overall yield from dehydroepiandrosterone.
Escherichia coli glucuronylsynthase: An engineered enzyme for the synthesis of β-glucuronides
Wilkinson, Shane M.,Liew, Chu W.,Mackay, Joel P.,Salleh, Hamzah M.,Withers, Stephen G.,McLeod, Malcolm D.
supporting information; experimental part, p. 1585 - 1588 (2009/04/10)
The glycosynthase derived from E. coli β-glucuronidase catalyzes the glucuronylation of a range of primary, secondary, and aryl alcohols with moderate to excellent yields. The procedure provides an efficient, stereoselective, and scalable single-step synthesis of β-glucuronides under mild conditions.
