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Literature DB >> 12599468

Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.

James D Pennington¹, Howard J Williams, Arthur R Salomon, Gary A Sulikowski.

Abstract

[formula: see text] Isoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.

Entities: Chemical Species

Mesh：

Substances：

Year: 2002 PMID： 12599468 DOI： 10.1021/ol026829v

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

14 in total

1. Profiling of rotavirus 3'UTR-binding proteins reveals the ATP synthase subunit ATP5B as a host factor that supports late-stage virus replication.

Authors: Lili Ren; Siyuan Ding; Yanhua Song; Bin Li; Muthukumar Ramanathan; Julia Co; Manuel R Amieva; Paul A Khavari; Harry B Greenberg
Journal: J Biol Chem Date: 2019-02-15 Impact factor: 5.157

2. Biosynthesis of the Apoptolidins in Nocardiopsis sp. FU 40.

Authors: Yu Du; Dagmara K Derewacz; Sean M Deguire; Jesse Teske; Jacques Ravel; Gary A Sulikowski; Brian O Bachmann
Journal: Tetrahedron Date: 2011-09-02 Impact factor: 2.457

3. Fluorescent probes of the apoptolidins and their utility in cellular localization studies.

Authors: Sean M DeGuire; David C Earl; Yu Du; Brenda A Crews; Aaron T Jacobs; Alessandro Ustione; Cristina Daniel; Katherine M Chong; Lawrence J Marnett; David W Piston; Brian O Bachmann; Gary A Sulikowski
Journal: Angew Chem Int Ed Engl Date: 2014-11-27 Impact factor: 15.336

Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.

1. Profiling of rotavirus 3'UTR-binding proteins reveals the ATP synthase subunit ATP5B as a host factor that supports late-stage virus replication.

2. Biosynthesis of the Apoptolidins in Nocardiopsis sp. FU 40.

3. Fluorescent probes of the apoptolidins and their utility in cellular localization studies.

Review 4. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

5. Apoptolidins B and C: isolation, structure determination, and biological activity.

6. Light-induced isomerization of apoptolidin a leads to inversion of C2-C3 double bond geometry.

7. The use of fluorescently-tagged apoptolidins in cellular uptake and response studies.

8. Apoptolidins E and F, new glycosylated macrolactones isolated from Nocardiopsis sp.

9. An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts.

10. Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues.