Conformational Analysis of (+)‐Germacrene D‐4‐ol Using the Crystalline Sponge Method to Elucidate the Origin of its Instability
Abstract: Unsaturated cyclic terpenes often exhibit instability due to the proximation of C=C bonds in the cyclic skeleton, leading to nonenzymatic degradation. In this study, the crystalline sponge (CS) method was employed for the X‐ray conformational analysis of a minute amount of oily and cyclic terpene compound, (+)‐germacrene D‐4‐ol, which was produced by a terpene synthase OILTS under in vitro conditions. The CS method revealed a reactive conformation of the cyclic terpene with proximal double bonds. Under weakly acidic in vivo conditions, OILTS gave four pseudo‐natural products or artifacts. The CS method also elucidated the structures of these degraded compounds, proposing a degradation mechanism triggered by the transannular reactions.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Conformational Analysis of (+)‐Germacrene D‐4‐ol Using the Crystalline Sponge Method to Elucidate the Origin of its Instability ; day:21 ; month:06 ; year:2024 ; extent:5
Chemistry - a European journal ; (21.06.2024) (gesamt 5)
- Urheber
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Jung, Youngcheol
Mitsuhashi, Takaaki
Kageyama, Ko
Kikuchi, Takashi
Sato, Sota
Fujita, Makoto
- DOI
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10.1002/chem.202400512
- URN
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urn:nbn:de:101:1-2406221405549.493467638971
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 11:04 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Jung, Youngcheol
- Mitsuhashi, Takaaki
- Kageyama, Ko
- Kikuchi, Takashi
- Sato, Sota
- Fujita, Makoto
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