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Literature DB >> 14703369

Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol.

Marek Urbansky¹, Chad E Davis, Jacob D Surjan, Robert M Coates.

Abstract

[reaction: see text] Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from D-arabitol using a convenient benzylidene and tert-butyldimethylsilyl protection of polyhydroxylated intermediates. The new scheme offers a straightforward route to analogues and labeled forms.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 14703369 DOI： 10.1021/ol0362562

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

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Cited

11 in total

1. Total synthesis and structure revision of the marine metabolite palmerolide A.

Authors: Xin Jiang; Bo Liu; Sylvain Lebreton; Jef K De Brabander
Journal: J Am Chem Soc Date: 2007-04-26 Impact factor: 15.419

2. Probing phosphorylation by non-mammalian isoprenoid biosynthetic enzymes using (1)H-(31)P-(31)P correlation NMR spectroscopy.

Authors: Ananya Majumdar; Meha H Shah; J Kipchirchir Bitok; Maria E Hassis-LeBeau; Caren L Freel Meyers
Journal: Mol Biosyst Date: 2009-05-15

3. Characterization of the sugar alcohol-producing yeast Pichia anomala.

Authors: Guoqiang Zhang; Yuping Lin; Peng He; Lin Li; Qinhong Wang; Yanhe Ma
Journal: J Ind Microbiol Biotechnol Date: 2013-10-30 Impact factor: 3.346

4. Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate and kinetic studies of Mycobacterium tuberculosis IspF.

Authors: Prabagaran Narayanasamy; Hyungjin Eoh; Patrick J Brennan; Dean C Crick
Journal: Chem Biol Date: 2010-02-26

5. Synthesis and Evaluation of Fluoroalkyl Phosphonyl Analogues of 2- C-Methylerythritol Phosphate as Substrates and Inhibitors of IspD from Human Pathogens.

Authors: David Bartee; Michael J Wheadon; Caren L Freel Meyers
Journal: J Org Chem Date: 2018-06-11 Impact factor: 4.354

Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol.

1. Total synthesis and structure revision of the marine metabolite palmerolide A.

2. Probing phosphorylation by non-mammalian isoprenoid biosynthetic enzymes using (1)H-(31)P-(31)P correlation NMR spectroscopy.

3. Characterization of the sugar alcohol-producing yeast Pichia anomala.

4. Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate and kinetic studies of Mycobacterium tuberculosis IspF.

5. Synthesis and Evaluation of Fluoroalkyl Phosphonyl Analogues of 2- C-Methylerythritol Phosphate as Substrates and Inhibitors of IspD from Human Pathogens.

6. Effect of temperature on D-arabitol production from lactose by Kluyveromyces lactis.

7. Formal Synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol From D-(+)-Arabitol.

8. 2C-Methyl-d-erythritol 4-phosphate enhances and sustains cyclodiphosphate synthase IspF activity.

9. Synthesis and evaluation of stable substrate analogs as potential modulators of cyclodiphosphate synthase IspF.

10. ENANTIOMERIC SYNTHESIS OF 2-C-METHYL-D-ERYTHRITOL 2, 4-CYCLODIPHOSPHATE.