Liquid ion exchangers in paper chromatography of steroidal glucosiduronic acids, glucosiduronic esters and free steroids

Mattox, Vernon R.; Goodrich, June E.; Litwiller, Robert D.

doi:10.1016/s0021-9673(00)97485-5

Cited by 15 publications

(2 citation statements)

References 17 publications

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“…From previous chromatographic studies it may be implied that in the presence of a liquid ion-exchanger the extent to which the mobility of a steroidal glucosiduronate changes with a change in concentration of counterion is dependent on the number of carboxyl groups present in the conjugate (Mattox et al, 1975a). We utilized this technique to obtain preliminary evidence that the acid-labile conjugate (XII) Hatchedareasrepresentzonesthatcontainedthealdosterone 18f8-glucosiduronicacid.…”

Section: Isolation Ofthe Acid-labile Conjugatefrom Urinementioning

confidence: 99%

“…Liquid ion-exchangers (Mattox et al, , 1975a,b) were used for chromatography on paper and columns. For paper the solvent systems were: (K) 0.05M-Aliquat (in chloroform)/0.05M-KCl (in formamide); (L) 0.1 M-tetraheptylammonium acetate (in chloroform)/0.1 M-potassium acetate (in formamide); (M) 0.1 M-tetraheptylammonium acetate (in chloroform)/0.4M-potassium acetate (in formamide); (N) 0.05M-KCI (in water)/0.05M-Aliquat (in chloroform); (0) 0.1 M-KCI (in water)/0.05M-Aliquat (in chloroform); (P) 0.2 M-KCI (in water)/ 0.05M-Aliquat (in chloroform).…”

Section: Chromatographymentioning

confidence: 99%

See 1 more Smart Citation

Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone

Carpenter¹,

Mattox²

1976

Biochemical Journal

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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.

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Section: Isolation Ofthe Acid-labile Conjugatefrom Urinementioning

confidence: 99%

Section: Chromatographymentioning

confidence: 99%