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Literature DB >> 16438548

Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) from D-xylose.

Abstract

The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC(50) = 0.01 microg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16438548 PMCID： PMC4140561 DOI： 10.1021/jo051644y

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

8 in total

1. A Synthesis of (+)-Cyclophellitol from D-Xylose.

Authors: Frederick E. Ziegler; Yizhe Wang
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

2. Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B).

Authors: Pushpal Bhaket; Kay Morris; Christina S Stauffer; Apurba Datta
Journal: Org Lett Date: 2005-03-03 Impact factor: 6.005

3. Synthesis and conformational investigation of methyl 4a-carba-D-arabinofuranosides.

Authors: C S Callam; T L Lowary
Journal: J Org Chem Date: 2001-12-28 Impact factor: 4.354

4. Effect of Rho and ADP-ribosylation factor GTPases on phospholipase D activity in intact human adenocarcinoma A549 cells.

Authors: E Meacci; V Vasta; J P Moorman; D A Bobak; P Bruni; J Moss; M Vaughan
Journal: J Biol Chem Date: 1999-06-25 Impact factor: 5.157

1 in total

1. The first total synthesis of sporiolide A.

Authors: Yuguo Du; Qi Chen; Robert J Linhardt
Journal: J Org Chem Date: 2006-10-27 Impact factor: 4.354

1 in total

Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) from D-xylose.

1. A Synthesis of (+)-Cyclophellitol from D-Xylose.

2. Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B).

3. Synthesis and conformational investigation of methyl 4a-carba-D-arabinofuranosides.

4. Effect of Rho and ADP-ribosylation factor GTPases on phospholipase D activity in intact human adenocarcinoma A549 cells.

5. Complex peptidyl nucleoside antibiotics: efficient syntheses of the glycosyl nucleoside amino acid cores.

6. Stereoselective synthesis of (+)-boronolide.

7. Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.

8. Sphingosine 1-phosphate induces arachidonic acid mobilization in A549 human lung adenocarcinoma cells.

1. The first total synthesis of sporiolide A.