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Synthesis and structural study of carbocyclic analogues of 1,2-disubstituted nucleosides

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Abstract

The compounds (±)-cis- and (±)-trans-9-[(2-hydroxymethyl) cyclopentyl]guanine (1 and 2 respectively) were efficiently synthesized by the construction of the purine base on the primary amino group of cis- and trans-2-aminocyclopentylmethanol. The 3D structures of these two 1,2-disubstituted carbanucleosides in DMSO were determined using molecular dynamics calculations with experimental NMR restraints on the basis of the information obtained from a ROESY spectrum. These structures were compared with those obtained in vacuo using molecular dynamics and AM1 semiempirical calculations. The global structures of the two compounds are very similar in the two environments studied, meaning that the structural determination in the gas phase can be extrapolated to molecular simulation studies in solution for compounds of this type.

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Authors and Affiliations

  1. Department of Physical Chemistry, Faculty of Chemical Sciences, University of Valencia, Valencia, Spain

    M. Carmen Martinez-Bisbal & Bernardo Celda

  2. Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782, Santiago de Compostela, Spain

    Santiago Vilar, Marta Teijeira, Eugenio Uriarte & Lourdes Santana

Authors
  1. M. Carmen Martinez-Bisbal
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  2. Santiago Vilar
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  3. Marta Teijeira
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  4. Bernardo Celda
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  5. Eugenio Uriarte
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  6. Lourdes Santana
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Correspondence to Santiago Vilar.

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Martinez-Bisbal, M.C., Vilar, S., Teijeira, M. et al. Synthesis and structural study of carbocyclic analogues of 1,2-disubstituted nucleosides. Struct Chem 17, 465–471 (2006). https://doi.org/10.1007/s11224-006-9068-3

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  • DOI: https://doi.org/10.1007/s11224-006-9068-3

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