The molecular structure of an aldosterone 18-glucopyranosiduronate

Charles M. Weeks; Douglas C. Rohrer; William L. Duax

doi:10.1016/0022-4731(76)90075-3

The molecular structure of an aldosterone 18-glucopyranosiduronate

Charles M. Weeks
, Douglas C. Rohrer
, William L. Duax

Department of Structural Biology

Hauptman-Woodward Medical Research Institute, Inc.

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

The crystal and molecular structure of aldosterone 18R-α-d-glucopyranosiduronic acid tetraacetate methyl ester was determined by X-ray analysis in order to ascertain the stereochemistry of the glycosidic bond and the configuration at C(18). The C(18) stereochemistry was found to be the same as that observed in the crystal structure of aldosterone monohydrate, and the C-ring has similar strain as shown by the C(11)-C(12)-C(13) valency angle of 98°. The sugar ring, which has a ⁴C₁ conformation, is approximately parallel to the steroid nucleus and is located above the aldosterone 17β-side chain.

Original language	English
Pages (from-to)	545-551
Number of pages	7
Journal	Journal of Steroid Biochemistry
Volume	7
Issue number	8
DOIs	https://doi.org/10.1016/0022-4731(76)90075-3
State	Published - Aug 1976

Keywords

18-epoxy-21-acetoxy-3
18R-α-d-glucosiduronic acid tetraacetate methyl ester will be used as an abbrevi-ation for methyl [(18R)-11β
2
20-dioxo-4-pregnen-18-yl
3
4-tri-O-acetyl-α-d-glucopyranosid] uronate throughout the remainder of this paper

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10.1016/0022-4731(76)90075-3

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title = "The molecular structure of an aldosterone 18-glucopyranosiduronate",

abstract = "The crystal and molecular structure of aldosterone 18R-α-d-glucopyranosiduronic acid tetraacetate methyl ester was determined by X-ray analysis in order to ascertain the stereochemistry of the glycosidic bond and the configuration at C(18). The C(18) stereochemistry was found to be the same as that observed in the crystal structure of aldosterone monohydrate, and the C-ring has similar strain as shown by the C(11)-C(12)-C(13) valency angle of 98°. The sugar ring, which has a 4C1 conformation, is approximately parallel to the steroid nucleus and is located above the aldosterone 17β-side chain.",

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author = "Weeks, \{Charles M.\} and Rohrer, \{Douglas C.\} and Duax, \{William L.\}",

year = "1976",

month = aug,

doi = "10.1016/0022-4731(76)90075-3",

language = "English",

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pages = "545--551",

journal = "Journal of Steroid Biochemistry",

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T1 - The molecular structure of an aldosterone 18-glucopyranosiduronate

AU - Weeks, Charles M.

AU - Rohrer, Douglas C.

AU - Duax, William L.

PY - 1976/8

Y1 - 1976/8

N2 - The crystal and molecular structure of aldosterone 18R-α-d-glucopyranosiduronic acid tetraacetate methyl ester was determined by X-ray analysis in order to ascertain the stereochemistry of the glycosidic bond and the configuration at C(18). The C(18) stereochemistry was found to be the same as that observed in the crystal structure of aldosterone monohydrate, and the C-ring has similar strain as shown by the C(11)-C(12)-C(13) valency angle of 98°. The sugar ring, which has a 4C1 conformation, is approximately parallel to the steroid nucleus and is located above the aldosterone 17β-side chain.

AB - The crystal and molecular structure of aldosterone 18R-α-d-glucopyranosiduronic acid tetraacetate methyl ester was determined by X-ray analysis in order to ascertain the stereochemistry of the glycosidic bond and the configuration at C(18). The C(18) stereochemistry was found to be the same as that observed in the crystal structure of aldosterone monohydrate, and the C-ring has similar strain as shown by the C(11)-C(12)-C(13) valency angle of 98°. The sugar ring, which has a 4C1 conformation, is approximately parallel to the steroid nucleus and is located above the aldosterone 17β-side chain.

KW - 18-epoxy-21-acetoxy-3

KW - 18R-α-d-glucosiduronic acid tetraacetate methyl ester will be used as an abbrevi-ation for methyl [(18R)-11β

KW - 2

KW - 20-dioxo-4-pregnen-18-yl

KW - 3

KW - 4-tri-O-acetyl-α-d-glucopyranosid] uronate throughout the remainder of this paper

UR - https://www.scopus.com/pages/publications/0016989471

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DO - 10.1016/0022-4731(76)90075-3

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AN - SCOPUS:0016989471

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JO - Journal of Steroid Biochemistry

JF - Journal of Steroid Biochemistry

IS - 8

ER -

The molecular structure of an aldosterone 18-glucopyranosiduronate

Abstract

Keywords

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