Literature DB >> 18776494

What are the consequences of freezing the anomeric effect in nucleosides?

Victor E Marquez1, Guangyu Sun, Maqbool A Siddiqui, Yi-Chien Lee, Joseph J Barchi, Igor V Filippov, Nicklaus A Landsman, James A Kelley.   

Abstract

The consequences of freezing the orientation of the oxygen's lone pair orbitals--which determines whether the anomeric effect is operative or not--were studied theoretically and experimentally in two oxobicyclo-[3.1.0]hexane nucleosides (1 and 2). The results showed significant differences in the properties of these molecules, which correlated with the magnitude of the n2 --> sigma * delocalization.

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Year:  2008        PMID: 18776494      PMCID: PMC2700545          DOI: 10.1093/nass/nrn275

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


  1 in total

1.  Using conformationally locked nucleosides to calibrate the anomeric effect: Implications for glycosyl bond stability.

Authors:  Hyung Ryong Moon; Maqbool A Siddiqui; Guangyu Sun; Igor V Filippov; Nicholas A Landsman; Yi-Chien Lee; Kristie M Adams; Joseph J Barchi; Jeffrey R Deschamps; Marc C Nicklaus; James A Kelley; Victor E Marquez
Journal:  Tetrahedron       Date:  2010-08-21       Impact factor: 2.457

  1 in total

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