Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol

Di-Capua, S.; Jang, H.G.; Barasch, Dinorah; Halperin, Gideon; Deutsch, Joseph

doi:10.1016/s0168-1176(97)00034-7

Cited by 2 publications

(4 citation statements)

References 9 publications

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“…However, the [M + H − H 2 O] + /[M + H] + ratio of the βOH isomer 2 was found to be five times higher than that of αOH isomers 1. The ratio concludes the results reported by Di‐Capua et al 9…”

Section: Resultssupporting

confidence: 90%

“…In most of the isomeric alcohols, the extent of water elimination expressed as the relative abundance of [M − H 2 O] + ions is used as an additional aid for the determination of the stereochemistry of the hydroxyl group. The [M − H 2 O] + /[M] + ratio of the 3βOH isomer (17β‐tetrahydropyranyloxy‐19‐norandrostan‐3β‐ol) was found to be three to four times higher than that of 3αOH isomers 9. Similarly, The [M + H − H 2 O] + /[M + H] + ratio of the βOH isomer 2 was found to be five times higher than that of αOH isomer 1.…”

Section: Resultsmentioning

confidence: 96%

“…MS usually does not allow differentiation of stereoisomers. However, the stereochemistry of 17β‐tetrahydropyranyloxy‐19‐norandrostan‐3β‐ol was determined by mass spectral measurements of the extent of water elimination from the molecular ion under EI conditions 9. In MS, hydrogen–deuterium (H/D) exchange is an extremely important tool for determining structures.…”

Section: Introductionmentioning

confidence: 99%

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Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Kanojiya

Yadav

2008

J. Mass Spectrom.

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Different stereoisomers of active molecules often cause different physiological responses and hence pose a challenge for their identification. This study involves perceptive fragmentation behavior of newly isolated cassane butenolides, caesalpinolide A [1] and caesalpinolide B [2] (epimeric at the hemiketal position) by tandem MS. The electrospray ionization-mass spectrometry (ESI-MS)/collision-induced dissociation (CID; ESI-MS(2) and ESI-IT-MS(n)) were investigated. The effect of orientations of hemiketal hydroxyl at C-12 was clearly observed in the mass spectrum. Tandem mass spectra of 1, 1(A) or 2, 2(A) show stereospecific fragmentation resulting in significant abundance dissimilarity of [MH - H(2)O](+) as well as differences in fragmentation pathway. Both of these pathways seem to be influenced by the stereochemistry of the molecule. The differentiation can be clearly visualized from the [M + H - H(2)O](+)/[M + H](+) ratio of the two isomers where beta-isomer 2 was found to be five times higher than that of alpha-isomer 1 in full scan liquid chromatography-electrospray ionization mass spectrometry(LC-ESI-MS). In high-energy CID, the mass fingerprint of 1, 2, 1(A), and 2(A) was found to be different from one another.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Kanojiya

Yadav

2008

J. Mass Spectrom.

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“…(a) The synthesis of 3α-hydroxy estrane moieties was carried out using a modification of a published procedure . The starting material was estrane-4-en-3,17-dione (Scheme ) which, by hydrogenation on RhCl 3 hydrate, produced a 5β-estrane-3,17- dione (compound 2 ), with cis stereochemistry (80%) at the A/B ring junction. , Both ketone groups were protected as ethylene ketal, yielding compound 3 . After selective removal of the ketal at the 3 position by iodine in acetone 35 (compound 4 ), the ketone was treated with NaBH 4 in THF/methanol, selectively producing the 3α-hydroxy-5β-estran-17-one ethylene ketal (compound 5 ).…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol: An Anti-Digoxin Agent with a Novel Mechanism of Action

et al. 2005

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The synthesis and some pharmacological properties of 4-(3'alpha-15'beta-dihydroxy-5beta-estran-17'beta-yl)furan-2-methyl alcohol (16) have been described. The compound was synthesized by reacting a synthetic 3alpha- benzyloxy-5beta-estr-15-en-17-one with the ethylene acetal of 4-bromo-2-furancarboxyaldehyde, followed by hydrolysis of the ethylene acetal and reduction of the aldehyde. Despite its resemblance to the structure of cardiac steroids (CS), 16 does not bind to the CS receptor on Na(+),K(+)-ATPase and does not increase the force of contraction of heart muscle. However, 16 inhibited the digoxin-induced increase in the force of contraction and arrhythmias in guinea pig papillary muscle and human atrial appendages. The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action.

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Mass spectral determination of the configuration of 17β-tetrahydropyranyloxy-19-norandrostan-3β-ol

Cited by 2 publications

References 9 publications

Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

4-(3‘α15‘β-Dihydroxy-5‘β-estran-17‘β-yl)furan-2-methyl Alcohol: An Anti-Digoxin Agent with a Novel Mechanism of Action

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