131749-24-1Relevant articles and documents
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
Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites
Hintikka, Laura,Kuuranne, Tiia,Aitio, Olli,Thevis, Mario,Schaenzer, Wilhelm,Kostiainen, Risto
, p. 257 - 265 (2008/09/17)
Enzyme-assisted in vitro synthesis of eleven glucuronide-conjugated anabolic androgenic steroid (AAS) metabolites was performed using biphenyl-induced rat liver microsomal enzymes. The substrates within the study were the main compounds and metabolites detected in human urine after dosing of, e.g. metandienone, metenolone, methyltestosterone, nandrolone, and testosterone. Yields of glucuronidation reactions were 13-28% for most compounds, but significantly higher (77-78%) for the substrates with 4-ene-3-one double bond system of the steroid A-ring. Characterization of glucuronide-conjugated AAS structures was based on nuclear magnetic resonance spectroscopy (1H NMR) and on liquid chromatographic-mass spectrometric (LC-MS) and tandem mass spectrometric (LC-MS/MS) analyses in positive and negative ion mode electrospray ionization (ESI). Only minor differences were observed in optimal synthesis conditions between various substrates, which offer a potential to apply this in vitro assay as a default method for glucuronidation of new AAS substrates. The method allowed for a rapid production pathway of stereochemically pure AAS glucuronides in milligram amount, such as needed, e.g. in the development of analytical methods in forensic or pharmaceutical sciences, as well as in doping control.