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Literature DB >> 19552384

Combined chemical and biosynthetic route to access a new apoptolidin congener.

Victor P Ghidu¹, Ioanna Ntai, Jingqi Wang, Aaron T Jacobs, Lawrence J Marnett, Brian O Bachmann, Gary A Sulikowski.

Abstract

Glycosylation of a synthetic aglycone using precursor-directed biosynthesis is facilitated by a chemical ketosynthase "knockdown" of the apoptolidin producer Nocardiopsis sp. This synthetic approach facilitated the preparation of an unnatural disaccharide derivative of apoptolidin D that substantially restores cytotoxicity against H292 cells and deconvolutes the role of the decorating sugars in apoptolidin bioactivity.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2009 PMID： 19552384 PMCID： PMC2720611 DOI： 10.1021/ol901045v

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

27 in total

1. Total synthesis of apoptolidin: completion of the synthesis and analogue synthesis and evaluation.

Authors: K C Nicolaou; Yiwei Li; Kazuyuki Sugita; Holger Monenschein; Prasuna Guntupalli; Helen J Mitchell; Konstantina C Fylaktakidou; Dionisios Vourloumis; Paraskevi Giannakakou; Aurora O'Brate
Journal: J Am Chem Soc Date: 2003-12-17 Impact factor: 15.419

2. Facile synthetic access to and biological evaluation of the macrocyclic core of apoptolidin.

Authors: Paul A Wender; Orion D Jankowski; Elie A Tabet; Haruo Seto
Journal: Org Lett Date: 2003-06-26 Impact factor: 6.005

Review 3. Bioactive microbial metabolites.

Authors: János Bérdy
Journal: J Antibiot (Tokyo) Date: 2005-01 Impact factor: 2.649

Review 4. Mutasynthesis, chemobiosynthesis, and back to semi-synthesis: combining synthetic chemistry and biosynthetic engineering for diversifying natural products.

Authors: Jonathan Kennedy
Journal: Nat Prod Rep Date: 2007-09-04 Impact factor: 13.423

5. Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp.

Authors: J W Kim; H Adachi; K Shin-ya; Y Hayakawa; H Seto
Journal: J Antibiot (Tokyo) Date: 1997-07 Impact factor: 2.649

6. Chimeramycins: new macrolide antibiotics produced by hybrid biosynthesis.

Authors: S Omura; N Sadakane; Y Tanaka; H Matsubara
Journal: J Antibiot (Tokyo) Date: 1983-07 Impact factor: 2.649

Review 7. Apoptolidin: induction of apoptosis by a natural product.

Authors: Peter T Daniel; Ulrich Koert; Julia Schuppan
Journal: Angew Chem Int Ed Engl Date: 2006-01-30 Impact factor: 15.336

8. Apoptolidin A: total synthesis and partially glycosylated analogues.

Authors: Hermut Wehlan; Mario Dauber; M Teresa Mujica Fernaud; Julia Schuppan; Sonja Keiper; Rainer Mahrwald; M-Elisa Juarez Garcia; Ulrich Koert
Journal: Chemistry Date: 2006-09-25 Impact factor: 5.236

9. Apoptolidinone A: synthesis of the apoptolidin A aglycone.

Authors: Julia Schuppan; Hermut Wehlan; Sonja Keiper; Ulrich Koert
Journal: Chemistry Date: 2006-09-25 Impact factor: 5.236

10. Deoxysugars in bioactive natural products: development of novel derivatives by altering the sugar pattern.

Authors: Carmen Méndez; Andriy Luzhetskyy; Andreas Bechthold; José A Salas
Journal: Curr Top Med Chem Date: 2008 Impact factor: 3.295

6 in total

1. 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

2. 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