Linked Life Data

962850

Source:http://linkedlifedata.com/resource/pubmed/id/962850

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1976-10-29
pubmed:abstractText
1. After administration of 600mg of 3H-labelled aldosterone to human volunteers, 57 mg of homogeneous acid-labile conjugate was isolated from the urine and identified as aldosterone 18 beta-D-glucosiduronic acid. 2. Esterification and acetylation of the conjugate gave a tetra-acetate methyl ester, which, by measurement of the optical rotation and nuclear-magnetic-resonance spectrum, was shown to be a beta-glucosiduronate. This tetra-acetate methyl ester was synthesized in approx. 10% yield by the Koenigs-Knorr procedure. 3. Removal of the acetyl and methyl ester groups from the tetra-acetate methyl ester with alkali was accompanied by almost complete isomerization at C-17 to give 17-isoaldosterone 18 beta-D-glucosiduronic acid. 4. To prevent inversion at C-17 during removal of the acetate and ester groups of beta-glucosiduronate (a) the 3,20-disemicarbazone was prepared, (b) the acetate and ester groups were removed from the disemicarbazone by treatment with alkali, and (c) the semicarbazone groups were removed from the product at pH 2.0, and aldosterone 18 beta-D-glucosiduronic acid was obtained in 47% overall yield. 5. In the presence of components used to synthesize beta-glucosiduronate by the Koenigs-Knorr reaction this substance is converted slowly into the alpha-glucosiduronate; this conversion is responsible, in part, for the low yield of beta-glucosiduronate. 6. Two additional conjugates were obtained in the Koenigs-Knorr reaction; a provisional structure was assigned to one substrate. The other substance is a C-18 alpha-glucosiduronate. Removal of the acetyl and ester groups from C-18 alpha-glucosiduronate gave the alpha-glucosiduronic acid in 84% yield and the 17-isoaldosterone alpha-glucosiduronic acid in 12% yield. 7. The rate at which several types of beta-glucuronidase hydrolyse the foregoing steroidal alpha- and beta-glucosiduronic acids is given.
pubmed:commentsCorrections
http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-1137999, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-1150814, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-14189903, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-14230008, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-14416359, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-16590842, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-4643016, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-4789315, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-5019968, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-5085134, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-5642321, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-5781011, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-5812049, http://linkedlifedata.com/resource/pubmed/commentcorrection/962850-5855057
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jul
pubmed:issn
0264-6021
pubmed:author
pubmed:issnType
Print
pubmed:day
1
pubmed:volume
157
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1-14
pubmed:dateRevised
2009-11-18
pubmed:meshHeading
pubmed:year
1976
pubmed:articleTitle
Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.