Molecular and crystal structure of Sp-thymidin-3'-yl 4-thiothymidin-5'-yl methylphosphonate.
The molecular structure of one diastereomer of the dinucleoside methylphosphonate Tp(Me)sT (1) has been determined by X-ray diffraction methods. The crystal asymmetric unit contains one molecule of 1 and one methanol in an orthorhombic unit cell of dimensions a = 13.241(4), b = 13.844(3), c = 14.944(7) A, space group P2(1)2(1)2(1). Both pyrimidine bases in 1 are oriented anti relative to the 2'-deoxyribose rings, and the sugar conformations are 2E and 2(3)T in the 4-thiothymidine and thymidine moieties, respectively. The deoxyribose-phosphonate backbone has an extended conformation with the bases completely unstacked and almost parallel. The absolute configuration at the phosphorus center in 1 is Sp.
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
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D002241:Carbohydrates / Q000737:chemistry; D003855:Deoxyribose / Q000737:chemistry; D015226:Dinucleoside Phosphates / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction
D002241:Carbohydrates; D015226:Dinucleoside Phosphates; D006571:Heterocyclic Compounds; D009943:Organophosphorus Compounds; C083207:thymidin-3'-yl-4-thiothymidin-5'-yl methylphosphonate; C032627:methylphosphonic acid; D003855:Deoxyribose