Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2014 Aug 28;12(32):6208-14.
doi: 10.1039/c4ob00984c. Epub 2014 Jul 8.

The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope

Paul Ma  1 , Nicholas Kanizaj, Shu-Ann Chan, David L Ollis, Malcolm D McLeod
Affiliations

The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope

Paul Ma et al. Org Biomol Chem. .

Abstract

A library of steroid glucuronides was prepared using the glucuronylsynthase derived from Escherichia coliβ-glucuronidase, followed by purification using solid-phase extraction. A representative range of steroid substrates were screened for synthesis on the milligram scale under optimised conditions with conversions dependent on steroid substitution and stereochemistry. Epiandrosterone (3β-hydroxy-5α-androstan-17-one) provided the highest conversion of 90% (84% isolated yield). The previously unreported glucuronide conjugates of methandriol (17α-methylandrost-5-ene-3β,17β-diol), cholest-5-ene-3β,25-diol and the designer steroid trenazone (17β-hydroxyestra-4,9-dien-3-one) were prepared on a multi-milligram scale suitable for characterisation by (1)H and (13)C NMR spectroscopy. The glucuronide conjugate of d5-etiocholanolone (2,2,3,4,4-d5-3α-hydroxy-5β-androstan-17-one), a target developed by the World Anti-Doping Agency as a certified reference material, was also prepared on a milligram scale. The improved E. coli glucuronylsynthase method provides for the rapid synthesis and purification of steroid glucuronides on a scale suitable for a range of analytical applications.

PubMed Disclaimer

Similar articles

See all similar articles

Cited by

  • Comparison of Toxicities among Different Bumped Kinase Inhibitor Analogs for Treatment of Cryptosporidiosis.
    Hulverson MA, Choi R, Schaefer DA, Betzer DP, McCloskey MC, Whitman GR, Huang W, Lee S, Pranata A, McLeod MD, Marsh KC, Kempf DJ, LeRoy BE, Zafiratos MT, Bielinski AL, Hackman RC, Ojo KK, Arnold SLM, Barrett LK, Tzipori S, Riggs MW, Fan E, Van Voorhis WC. Hulverson MA, et al. Antimicrob Agents Chemother. 2023 Apr 18;67(4):e0142522. doi: 10.1128/aac.01425-22. Epub 2023 Mar 15. Antimicrob Agents Chemother. 2023. PMID: 36920244 Free PMC article.

Publication types

MeSH terms

LinkOut - more resources

-