| WYE-120318, a ring contraction product of methylnaltrexone, and structure revision of coniothyrione. | |
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MedLine Citation:
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PMID: 23135875 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. Copyright © 2012 John Wiley & Sons, Ltd. |
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Authors:
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Fangming Kong; Tianmin Zhu; Weitao Pan; Russ Tsao; Thomas G Pagano; Bao Nguyen; Brian Marquez |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-11-8 |
Journal Detail:
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Title: Magnetic resonance in chemistry : MRC Volume: - ISSN: 1097-458X ISO Abbreviation: Magn Reson Chem Publication Date: 2012 Nov |
Date Detail:
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Created Date: 2012-11-8 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9882600 Medline TA: Magn Reson Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2012 John Wiley & Sons, Ltd. |
Affiliation:
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Structure Elucidation Group, Pfizer Worldwide Research and Development, 445 East Point Road, Groton, CT, 06340, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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