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231224s2012 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.3892
|2 doi
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|a pubmed24n0741.xml
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|a (DE-627)NLM222466693
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|a (NLM)23135875
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|a DE-627
|b ger
|c DE-627
|e rakwb
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|a eng
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|a Kong, Fangming
|e verfasserin
|4 aut
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|a WYE-120318, a ring contraction product of methylnaltrexone, and structure revision of coniothyrione
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|c 2012
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
|b c
|2 rdamedia
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|a ƒa Online-Ressource
|b cr
|2 rdacarrier
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|a Date Completed 26.04.2013
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|a Date Revised 25.11.2016
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Copyright © 2012 John Wiley & Sons, Ltd.
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|a A contracted ring degradation product, WYE-120318 (compound 2), was discovered during the development phase for methylnaltrexone bromide (compound 1) drug substance. The compound was isolated by high-performance liquid chromatography fractionation, and its structure was determined by spectroscopic data analyses. WYE-120318 is formed from methylnaltrexone through a benzyl-benzilic acid type rearrangement reaction to yield an α-hydroxy-cyclopentanecarboxylic acid substructure. The proposed structure and the formation mechanism are confirmed by the synthesis of WYE-120318 from methylnaltrexone (compound 1). A similar benzyl-benzilic acid type rearrangement reaction can be envisioned as the biological origin of remisporine A (compound 3), a naturally occurring cyclopentadienyl compound that autocatalytically dimerizes to remisporine B (compound 4). The structure of remisporine A was deduced from its dimer 4. Coniothyione (compound 5) can be considered as the first example of a stable natural product bearing the remisporine A skeleton. However, the regiochemistry of the chlorosubstitution in the coniothyrione structure needs to be revised to compound 6 on the basis of the nuclear magnetic resonance data and biogenesis analysis
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|a Journal Article
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|a Chromones
|2 NLM
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|a Quaternary Ammonium Compounds
|2 NLM
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|a WYE-120318
|2 NLM
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|a coniothyrione
|2 NLM
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|a methylnaltrexone
|2 NLM
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|a 0RK7M7IABE
|2 NLM
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| 650 |
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|a Naltrexone
|2 NLM
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| 650 |
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|a 5S6W795CQM
|2 NLM
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| 700 |
1 |
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|a Zhu, Tianmin
|e verfasserin
|4 aut
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| 700 |
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|a Pan, Weitao
|e verfasserin
|4 aut
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| 700 |
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|a Tsao, Russ
|e verfasserin
|4 aut
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| 700 |
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|a Pagano, Thomas G
|e verfasserin
|4 aut
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|a Nguyen, Bao
|e verfasserin
|4 aut
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|a Marquez, Brian
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 50(2012), 12 vom: 25. Dez., Seite 829-33
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
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|g volume:50
|g year:2012
|g number:12
|g day:25
|g month:12
|g pages:829-33
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|u http://dx.doi.org/10.1002/mrc.3892
|3 Volltext
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