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-acetoxy-androstane-3alpha,17beta-diol 9, 11alpha-hydroxyprogesterone 10, and 3-benzoylestradiol 11. These were first glucuronidated using the Schmidt trichloroacetimidate method with variations in acyl substituent (viz. derivatives 2 and 3), Lewis acid catalyst and order of addition. The results are contrasted with those obtained using our recently described glycosyl iodide donor 4, catalysed either by N-iodosuccinimide (NIS) or various metal salts.
Harding
John R
JR
AstraZeneca UK Ltd., Drug Metabolism and Pharmacokinetics Department, Mereside, Cheshire, UK.
King
Clare D
CD
Perrie
Jennifer A
JA
Sinnott
Deborah
D
Stachulski
Andrew V
AV
D000438:Alcohols / Q000737:chemistry*; D005965:Glucuronates / Q000737:chemistry*; D020719:Glucuronides / Q000737:chemistry*; D006031:Glycosylation; D007096:Imidoesters / Q000737:chemistry*; D015394:Molecular Structure; D013256:Steroids / Q000737:chemistry*
D000438:Alcohols; D005965:Glucuronates; D020719:Glucuronides; D007096:Imidoesters; D013256:Steroids; C511166:methyl 1-deoxy-1-iodo-2,3,4-tri-O-pivaloylglucopyranuronate