Aphidicolin: Its Chemistry and Biosynthesis

Hanson, James R.

doi:10.3184/174751918x15333061990467

Cited by 3 publications

(1 citation statement)

References 85 publications

(104 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Aphidicolin (Figure 1) is a potent DNA polymerase α inhibitor [39] and was explored in clinical trials by the European Organization for Research and Treatment of Cancer [40]. The unique configuration of its functional groups, together with its significant biological activity, makes the discovery of its analogs and the study of their chemistry rather interesting [41]. In this study, as a proof of concept, we explored the potential of CCSs in characterizing marine-derived natural products, especially isomers, using a group of aphidicolane metabolites obtained in our previous work as an example.…”

Section: Introductionmentioning

confidence: 99%

Ion Mobility-Derived Collision Cross-Sections Add Extra Capability in Distinguishing Isomers and Compounds with Similar Retention Times: The Case of Aphidicolanes

et al. 2022

View full text Add to dashboard Cite

The hyphenation of ion mobility spectrometry with high-resolution mass spectrometry has been widely used in the characterization of various metabolites. Nevertheless, such a powerful tool remains largely unexplored in natural products research, possibly mainly due to the lack of available compounds. To evaluate the ability of collision cross-sections (CCSs) in characterizing compounds, especially isomeric natural products, here we measured and compared the traveling-wave IMS-derived nitrogen CCS values for 75 marine-derived aphidicolanes. We established a CCS database for these compounds which contained 227 CCS values of different adducts. When comparing the CCS differences, 36 of 57 pairs (over 60%) of chromatographically neighboring compounds showed a ΔCCS over 2%. What is more, 64 of 104 isomeric pairs (over 60%) of aphidicolanes can be distinguished by their CCS values, and 13 of 18 pairs (over 70%) of chromatographically indistinguishable isomers can be differentiated from the mobility dimension. Our results strongly supported CCS as an important parameter with good orthogonality and complementarity with retention time. CCS is expected to play an important role in distinguishing complex and diverse marine natural products.

show abstract

Section: Introductionmentioning

confidence: 99%

Ion Mobility-Derived Collision Cross-Sections Add Extra Capability in Distinguishing Isomers and Compounds with Similar Retention Times: The Case of Aphidicolanes

et al. 2022

View full text Add to dashboard Cite

show abstract

Effect of Tether Length on endo/exo Stereoselectivity in Alkene–Arene meta‐Photocycloaddition Reactions towards the Aphidocolin/Stemodin Scaffolds

Alshammari,

Boyd,

Greaves

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

Intramolecular alkene‐arene meta‐photocycloadditions are powerful transformations that use the enhanced reactivity of photoexcited benzene rings to facilitate addition of an alkene 1,3 across donor groups and form complex three‐dimensional fused‐ring systems from readily accessible starting materials. Intramolecular examples have traditionally been restricted to 3‐membered tethers, with cycloaddition resulting from exo‐conformation. However, by judicious tether design we have demonstrated that a 4‐membered tether can also proceed in good yield; interestingly, via an endo‐exciplex (1.2:1) enabling access to both natural product skeletons and interesting scaffolds for medicinal chemistry research.

show abstract