Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

Microbial hydroxylation of acetylaminosteroids

H L Holland1, G Lakshmaiah, P L Ruddock

  • 1Department of Chemistry, Brock University, St. Catharines, Ontario, Canada. holland@chemiris.labs.brocku.ca

Steroids
|September 4, 1998
PubMed
Summary
This summary is machine-generated.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Biotransformation of beta-ketosulfides to produce chiral beta-hydroxysulfoxides.

Journal of industrial microbiology & biotechnology·2003
Same author

Biotransformation of organic sulfides.

Natural product reports·2001
Same author

Enzymatic hydroxylation reactions.

Current opinion in biotechnology·2000
Same author

The effect of 4beta and 19 ester functionalities on some electrophilic addition reactions of delta5-steroids.

Steroids·1999
Same author

Recent advances in applied and mechanistic aspects of the enzymatic hydroxylation of steroids by whole-cell biocatalysts.

Steroids·1999
Same author

Enantioselective synthesis and pharmacological evaluation of a new type of verapamil analog with hypotensive and calcium antagonist activities.

Pharmaceutical research·1999

Microbial biotransformation of steroids using Aspergillus ochraceus and Bacillus megaterium yielded specific hydroxylated products. Steroid structure influenced hydroxylation sites, demonstrating microbial metabolism adaptability.

Area of Science:

  • Microbiology
  • Biochemistry
  • Organic Chemistry

Background:

  • Steroid biotransformation is crucial for synthesizing modified steroids.
  • Microorganisms possess enzymes capable of hydroxylating steroid structures.
  • Understanding microbial hydroxylation patterns aids in drug development and metabolic studies.

Purpose of the Study:

  • To investigate the microbial biotransformation of acetylamino steroids.
  • To identify hydroxylation products generated by specific microorganisms.
  • To determine the influence of substrate structure on hydroxylation regioselectivity.

Main Methods:

  • Incubation of acetylamino steroids with Aspergillus ochraceus, Bacillus megaterium, Curvularia lunata, and Rhizoputus arrhizus.
  • Analysis of reaction products to identify hydroxylated metabolites.

Related Experiment Videos

  • Comparison of hydroxylation patterns across different microbial species and substrates.

    • Main Results:

    • Aspergillus ochraceus and Bacillus megaterium produced 11 alpha- and 15 beta-hydroxylated products, respectively.
    • Curvularia lunata exhibited typical C-11 beta- and C-14 alpha-hydroxylation, with one instance of substrate-directed 7 alpha-hydroxylation.
    • Rhizoputus arrhizus showed predominant 6 beta- and 11 alpha-hydroxylation, with regioselectivity influenced by substrate substitution.

    Conclusions:

    • Microbial hydroxylation of acetylamino steroids is feasible using common steroid-hydroxylating microorganisms.
    • The substitution pattern of the steroid substrate plays a significant role in directing the site and range of hydroxylation.
    • These findings contribute to the understanding of microbial steroid metabolism and offer potential for novel steroid derivative synthesis.