Literature DB >> 18776534

Synthesis of conformationally locked carbocyclic nucleoside phosphonates to probe the active site of HIV-1 RT.

Hisao Saneyoshi1, B Christie Vu, Stephen H Hughes, Paul L Boyer, Stefan G Sarafianos, Victor E Marquez.   

Abstract

The conformationally locked carbocyclic nucleoside phosphonates 2 and 2' and key intermediates for the synthesis of 3 and 3' were prepared from a chiral cyclopentene derivative and epicholorohydrine, respectively. The structure of the nucleoside precursor 6 was confirmed by X-ray crystallography. These carbocyclic nucleoside phosphonates were designed to probe their binding interactions at the active site of HIV-1-RT.

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Year:  2008        PMID: 18776534      PMCID: PMC2727548          DOI: 10.1093/nass/nrn315

Source DB:  PubMed          Journal:  Nucleic Acids Symp Ser (Oxf)        ISSN: 0261-3166


  4 in total

1.  Deoxythreosyl phosphonate nucleosides as selective anti-HIV agents.

Authors:  Tongfei Wu; Matheus Froeyen; Veerle Kempeneers; Christophe Pannecouque; Jing Wang; Roger Busson; Erik De Clercq; Piet Herdewijn
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

2.  Acyclic nucleoside phosphonates: past, present and future. Bridging chemistry to HIV, HBV, HCV, HPV, adeno-, herpes-, and poxvirus infections: the phosphonate bridge.

Authors:  E De Clercq
Journal:  Biochem Pharmacol       Date:  2006-09-19       Impact factor: 5.858

Review 3.  Synthesis and biological activity of phosphonated nucleosides: part 1. Furanose, carbocyclic and heterocyclic analogues.

Authors:  Anna Piperno; Maria A Chiacchio; Daniela Iannazzo; Roberto Romeo
Journal:  Curr Med Chem       Date:  2006       Impact factor: 4.530

4.  Cyclopropane-annelated azaoligoheterocycles by Ti-mediated intramolecular reductive cyclopropanation of cyclic amino Acid amides.

Authors:  Martina Gensini; Armin de Meijere
Journal:  Chemistry       Date:  2004-02-06       Impact factor: 5.236

  4 in total
  2 in total

1.  Synthesis of conformationally locked L-deoxythreosyl phosphonate nucleosides built on a bicyclo[3.1.0]hexane template.

Authors:  Hisao Saneyoshi; Jeffrey R Deschamps; Victor E Marquez
Journal:  J Org Chem       Date:  2010-10-21       Impact factor: 4.354

2.  Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors:  Cheng Ji; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

  2 in total

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