Literature DB >> 10793718

Nucleoside conformations. XVII. A PMR study of 2'-anhydronucleosides and comparison with X-ray data.

W Guschlbauer, T D Son, M Blandin, J C Catlin.   

Abstract

A series of 2'-cyclo-nucleosides (2,2'-O-anhydro-uridine, -N(3)-uridine and cytidine and 8,2'-S-anhydro-guanosine) have been studied by PMR in DMSO and D(2)O. As expected these compounds are quite rigid, but their solution conformation is considerably different from that observed in single crystal x-ray studies. While the pyrimidine cyclonucleosides in the crystal form show a C(4')-endo conformation (pseudorotational phase angle P=212 degrees to 233 degrees ), their solution conformation is C(1')-exo (P=130 degrees to 138 degrees ) and the cyclothioguanosine shows a closely similar one (P=112 degrees ). Exocyclic rotamer distribution is different in the various compounds.

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Year:  1974        PMID： 10793718      PMCID： PMC343389          DOI： 10.1093/nar/1.7.855

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  13 in total

1.  Nucleosides. XXXIX. 2'-deoxy-2'-fluorocytidine, 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-4-iminopyrimidine, and related derivatives.

Authors:  I L Doerr; J J Fox
Journal:  J Org Chem       Date:  1967-05       Impact factor: 4.354

2.  Conformation of nucleosides: the comparison of an x-ray diffraction and proton nmr study of 5',2-O-cyclo, 2',3'-O-isopropylidene uridine.

Authors:  P C Manor; W Saenger; D B Davies; K Jankowski; A Rabczenko
Journal:  Biochim Biophys Acta       Date:  1974-04-10

3.  Nucleoside conformations. 8. Conformation of guanosine 2'-phosphate in aqueous solution by proton magnetic resonance spectroscopy.

Authors:  T D Son; J Thiéry; W Guschlbauer; J J Dunand
Journal:  Biochim Biophys Acta       Date:  1972-10-27

4.  Studies on the Vilsmeier-Haack reaction. IV. Convenient synthesis of 2,2'-anhydro-1- -D-arabinofuranosylcytosine (2,2'-cyclocytidine) and its derivatives.

Authors:  K Kikugawa; M Ichino
Journal:  J Org Chem       Date:  1972-01-28       Impact factor: 4.354

5.  Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using the concept of pseudorotation.

Authors:  C Altona; M Sundaralingam
Journal:  J Am Chem Soc       Date:  1972-11-15       Impact factor: 15.419

6.  Nuclear magnetic resonance determination of syn and anti conformations in pyrimidine nucleosides.

Authors:  M P Schweizer; J T Witkowski; R K Robins
Journal:  J Am Chem Soc       Date:  1971-01-13       Impact factor: 15.419

7.  Synthesis of some pyrimidine 2'-amino-2'-deoxynucleosides.

Authors:  J P Verheyden; D Wagner; J G Moffatt
Journal:  J Org Chem       Date:  1971-01-29       Impact factor: 4.354

8.  Studies of the conformation and interaction in dinucleoside mono- and diphosphates by proton magnetic resonance.

Authors:  P O Ts'o; N S Kondo; M P Schweizer; D P Hollis
Journal:  Biochemistry       Date:  1969-03       Impact factor: 3.162

9.  Molecular conformation of orotidine, a naturally occurring nucleoside, in the syn conformation in aqueous solution.

Authors:  F E Hruska
Journal:  J Am Chem Soc       Date:  1971-04-07       Impact factor: 15.419

10.  Nucleotides. V. Purine ribonucleoside 2',3'-cyclic carbonates. Preparation and use for the synthesis of 5'-monosubstituted nucleosides.

Authors:  A Hampton; A W Nichol
Journal:  Biochemistry       Date:  1966-06       Impact factor: 3.162
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  2 in total

1.  Necleoside conformations. 19. Temperature and pH effects on the conformation of guanosine phosphates.

Authors:  T D Son; W Guschlbauer
Journal:  Nucleic Acids Res       Date:  1975-06       Impact factor: 16.971

2.  2'-Deoxy-2'-fluorouridine-5'-phosphate: an alternative substrate for thymidylate synthetase from Escherichia coli K12.

Authors:  F Wohlrab; T Haertlé; T Trichtinger; W Guschlbauer
Journal:  Nucleic Acids Res       Date:  1978-12       Impact factor: 16.971
  2 in total

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