1852-43-3

Usage

Definition

ChEBI: A steroid glucosiduronic acid having androsterone as the steroid component.

InChI:InChI=1/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)

Upstream product

• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 777038-38-7 α-D-glucuronyl fluoride 
• 53-41-8 cis-androsterone 
• 2616-64-0 uridine diphosphoglucuronic acid 
• 313948-92-4 methyl 1-deoxy-1-iodo-2,3,4-tri-O-pivaloyl-α-D-glucopyranuronate 
• 86448-91-1 methyl O¹,O²,O³,O⁴-tetra(2,2-dimethyl-1-oxopropyl)-β-D-glucuronate 
• 21085-73-4 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 65535-18-4 5α-androstane-3α,17β-diol-3-O-glucuronide 
• 6556-12-3 D-glucuronic acid 
• 53-41-8 cis-androsterone 

Relevant academic research and scientific papers

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

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

Glucuronidation of steroidal alcohols using iodosugar and imidate donors

We report a study of the glucuronidation of a number of important steroidal secondary alcohols. The alcohols studied are androsterone 7, epiandrosterone 8, 17-aceloxy-androstane-3α,17β-diol 9, 11α-hydroxyprogesterone 10, and 3-benzoylestradiol 11. These w

Mass spectrometry of steroid glucuronide conjugates. I. Electron impact fragmentation of 5α-/5β-androstan-3α-ol-17-one glucuronides, 5α-estran-3α-ol-17-one glucuronide and deuterium-labelled analogues

Owing to the developments of analytical instruments and interfaces (e.g. coupling high-performance liquid chromatography to mass spectrometry), there has been increased interest in new reference materials, for example in doping analysis with steroid glucuronide conjugates. The synthesized reference material has to pass several characterization steps including the use of gas chromatography/mass spectrometry (GC/MS) for its structure confirmation. In the present study, the fragmentation and mass spectrometric behaviour of several steroid glucuronide conjugates of endogenous and anabolic steroids after derivatization to pertrimethylsilylated products and to methyl ester pertrimethylsilylated products were investigated using GC/MS ion trap and GC/MS quadrupole instruments. The mass spectra of the derivatives of androsterone glucuronide, d5-androsterone glucuronide, epiandrosterone glucuronide, etiocholanolone glucuronide, 11β-hydroxy etiocholanolone glucuronide, 19-norandrosterone glucuronide, d4-19-norandrosterone glucuronide and 1α-methyl-5α-androstan-3α-ol-17-one glucuronide are presented and the origin of typical fragment ions of the glycosidic and steroidal moieties is proposed, based on different derivatization techniques including derivatization with d18-bistrimethylsilylacetamide, methyl ester and trimethylsilyl ester derivatization and selected reaction monitoring. Typical fragmentation patterns which are related to the steroid structure are discussed. Copyright

Glucosiduronidation and esterification of androsterone by human breast tumors in vitro

The metabolism of 3H-androsterone was studied in homogenates (fortified with uridine 5'-diphosphoglucuronic acid and andenosine 3'- phosphate 5'-phosphosulfate) of eighteen breast tumors, one muscle underlying the primary breast carcinoma and metastatic axillary lymph nodes from a patient with suspected primary breast cancer. The major metabolites identified were less polar than androsterone. On saponification these lipoidal derivatives afforded androsterone as the only product (3 to 48%). Unmetabolized androsterone and lesser quantities of epiandrosterone, 5α-andorstane-3α, 17β-diol and 5α-androstane-3,17-dione comprised the free steroid fraction. Androsterone glucosiduronate was isolated (0.17-4.1%) from eight breast tumor homogenates and fromthe node tissue incubation (17%). There was no apparent correlation between glucuronyltransferase activity and histolpathology or estrogen receptor content.