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Original Articles

31P NMR and Computational Studies on Stereochemistry of Conversion of Phosphoramidate Diesters into the Corresponding Phosphotriesters

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Pages 552-564 | Received 29 Mar 2011, Accepted 29 Apr 2011, Published online: 02 Sep 2011

REFERENCES

  • Slotin , L. A. 1977 . Current methods of phosphorylation of biological molecules . Synthesis , : 737 – 752 .
  • Stawinski , J. 1992 . “ Some aspects of H-phosphonate chemistry ” . In Handbook of Organophosphorus Chemistry , Edited by: Engel , R. 377 – 434 . New York : Marcel Dekker .
  • Beaucage , S. L. and Iyer , R. P. 1993 . The functionalization of oligonucleotides via phosphoramidite derivatives . Tetrahedron , 49 : 1925 – 1963 .
  • Nawrot , B. , Rebowska , B. , Michalak , O. , Bulkowski , M. , Blaziak , D. , Guga , P. and Stec , W. J. 2008 . 1,3,2-oxathiaphospholane approach to the synthesis of P-chiral stereodefined analogs of oligonucleotides and biologically relevant nucleoside polyphosphates . Pure Appl. Chem. , 80 : 1859 – 1871 .
  • Lemmen , P. , Richter , W. , Werner , B. , Karl , R. , Stumpf , R. and Ugi , I. 1993 . Five-membered cyclic phosphorylating reagents and related compounds . Synthesis , : 1 – 10 .
  • Efimov , V. A. , Molchanova , N. S. and Chakhmakhcheva , O. G. 2007 . Approach to the synthesis of natural and modified oligonucleotides by the phosphotriester method using O-nucleophilic intramolecular catalysis . Nucleosides, Nucleotides Nucleic Acids , 26 : 1087 – 1093 .
  • Nikolaides , N. and Ganem , B. 1990 . New chemistry of amines. 2. A convenient synthesis of phosphotriesters from phosphoramidates . Tetrahedron Lett. , 31 : 1113 – 1116 .
  • Luo , J. and Ganem , B. 1991 . A new method for transforming primary amines into phosphoric acid monoesters . Tetrahedron Lett. , 32 : 3145 – 3146 .
  • Emsley , J. and Hall , D. 1975 . The Chemistry of Phosphorus , 253 London : Harper & Row .
  • Nilsson , J. and Stawinski , J. 2004 . Controlling stereochemistry during oxidative coupling. Preparation of Rp or Sp phosphoramidates from one P-chiral precursor . Chem. Commun. , : 2566 – 2567 .
  • Nilsson , J. , Kraszewski , A. and Stawinski , J. 2005 . Chemical and stereochemical aspects of oxidative coupling of H-phosphonate and H-phosphonothioate diesters. Reactions with N,N-, N,O- and O,O-binucleophiles . Lett. Org. Chem. , 2 : 188 – 197 .
  • Kirby , A. J. and Warren , S. G. 1967 . The Organic Chemistry of Phosphorus , Amsterdam : Elsevier .
  • White , E. H. 1955 . The chemistry of the N-alkyl-N-nitrosoamides. I. Methods of preparation . J. Am. Chem. Soc. , 77 : 6008
  • White , E. H. 1955 . The chemistry of the N-alkyl-N-nitrosoamides. II. A new method for the deamination of aliphatic amines . J. Am. Chem. Soc. , 77 : 6011 – 6014 .
  • White , E. H. 1955 . The chemistry of the N-alkyl-N-nitrosoamides. III. Mechanism of the nitrogen elimination reaction . J. Am. Chem. Soc. , 77 : 6014 – 6022 .
  • Ohtsuka , E. , Murao , K. , Ubasawa , M. and Ikehara , M. 1970 . Transfer ribonucleic acids and related compounds. I. Synthesis of ribooligonucleotides using aromatic phosphoramidates as a protecting group . J. Am. Chem. Soc. , 92 : 3441 – 3445 .
  • Ohtsuka , E. , Murao , K. , Ubasawa , M. and Ikehara , M. 1969 . A new method for the synthesis of protected ribooligonucleotides with 3′-phosphate end groups . J. Am. Chem. Soc. , 91 : 1537 – 1538 .
  • Ohtsuka , E. , Shibahara , S. , Ono , T. , Fukui , T. and Ikehara , M. 1981 . Synthesis of deoxyribooligonucleotides by using aromatic phosphoramidates as the protecting group for the 3'-phospho ends . Heterocycles , 15 : 395 – 398 .
  • Ikehara , M. , Uesugi , S. and Fukui , T. 1967 . Studies of nucleosides and nucleotides. XXXI. Reaction of nitrous acid with mono- and di-esters of phosphoramidate . Chem. Pharm. Bull. , 15 : 440 – 447 .
  • Streitwieser , A. and Schaeffer , W. D. 1957 . Stereochemistry of the primary carbon. VII. The decomposition of N-(1-butyl-1-d)-N-nitrosoacetamide . J. Am. Chem. Soc. , 79 : 2893 – 2897 .
  • White , E. H. and Aufdermarsh , C. A. 1961 . N-nitrosoamides. IV. N-nitrosoamides of primary carbinamines . J. Am. Chem. Soc. , 83 : 1174 – 1178 .
  • Westheimer , F. H. 1968 . Pseudo-rotation in the hydrolysis of phosphate esters . Acc. Chem. Res. , 1 : 70 – 78 .
  • Hall , C. R. and Inch , T. D. 1980 . Phosphorus stereochemistry. Mechanistic implications of the observed stereochemistry of bond forming and breaking process at phosphorus in some 5- and 6-membered cyclic phosphorus esters . Tetrahedron , 36 : 2059 – 2095 .
  • Thatcher , G. R.J. and Kluger , R. 1989 . Mechanism and catalysis of nucleophilic substitution in phosphate esters . Adv. Phys. Org. Chem. , 25 : 99 – 265 .
  • Corriu , R. J.P. , Dutheil , J.-P. and Lanneau , G. 1981 . Analogies between silicon and phosphorus stereochemistry. II. Influence of the attacking anion upon the stereochemistry of nucleophilic displacement at tetrahedral phosphorus . Tetrahedron , 37 : 3681 – 3687 .
  • Corriu , R. J.P. , Lanneau , G. F. and Leclercq , D. 1983 . Silicon-phosphorus analogies rate controlling factors in SN2(P) reactions influence of the nucleophile for a given stereochemistry . Tetrahedron Lett. , 24 : 4323 – 4326 .
  • Corriu , R. J.P. 1986 . Nucleophilic substitutions at silcon and phosphorus. A comparison of controlling facfors . Phosphor Sulfur Silicon , 27 : 1 – 12 .
  • Nikolaides , N. , Schpor , I. and Ganem , B. 1998 . Conversion of amines to phospho esters: decyl diethyl phosphate . Organic Syntheses , 9 : 194
  • Tomoskozi , I. , Gacs-Baitz , E. and Otvos , L. 1995 . Stereospecific conversion of H-phosphonates into phosphoramidates. The use of vicinal carbon-phosphorus couplings for configurational determination of phosphorus . Tetrahedron , 51 : 6797 – 6804 .
  • Stawinski , J. and Thelin , M. 1991 . Nucleoside H-phosphonates. 13. Studies on 3H-1,2-benzodithiol-3-one derivatives as sulfurizing reagents for H-phosphonate and H-phosphonothioate diesters . J. Org. Chem. , 56 : 5169 – 5175 .
  • Zain , R. and Stawinski , J. 1996 . Nucleoside H-phosphonates. 17. Synthetic and 31P NMR studies on the preparation of dinucleoside H-phosphonothioates . J. Org. Chem. , 61 : 6617 – 6622 .
  • Stawinski , J. and Strömberg , R. 2004 . “ Di- and oligonucleotide synthesis using H-phosphonate chemistry ” . In Oligonucleotide Synthesis: Methods and Applications , Edited by: Herdewijn , P. Vol. 288 , 81 – 100 . Totowa , NJ : Humana Press .
  • Garegg , P. J. , Regberg , T. , Stawinski , J. and Strömberg , R. 1987 . Nucleosides H-phosphonates. V. The mechanism of hydrogenphosphonate diester formation using acyl chlorides as coupling agents in oligonucleotide synthesis by the hydrogenphosphonate approach . Nucleosides Nucleotides , 6 : 655 – 662 .
  • Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Scalmani , G. , Barone , V. , Mennucci , B. , Petersson , G. A. , Nakatsuji , H. , Caricato , M. , Li , X. , Hratchian , H. P. , Izmaylov , A. F. , Bloino , J. , Zheng , G. , Sonnenberg , J. L. , Hada , M. , Ehara , M. , Toyota , K. , Fukuda , R. , Hasegawa , J. , Ishida , M. , Nakajima , T. , Honda , Y. , Kitao , O. , Nakai , H. , Vreven , T. , Montgomery , J. A. Jr. , Peralta , J. E. , Ogliaro , F. , Bearpark , M. , Heyd , J. J. , Brothers , E. , Kudin , K. N. , Staroverov , V. N. , Kobayashi , R. , Normand , J. , Raghavachari , K. , Rendell , A. , Burant , J. C. , Iyengar , S. S. , Tomasi , J. , Cossi , M. , Rega , N. , Millam , J. M. , Klene , M. , Knox , J. E. , Cross , J. B. , Bakken , V. , Adamo , C. , Jaramillo , J. , Gomperts , R. , Stratmann , R. E. , Yazyev , O. , Austin , A. J. , Cammi , R. , Pomelli , C. , Ochterski , J. W. , Martin , R. L. , Morokuma , K. , Zakrzewski , V. G. , Voth , G. A. , Salvador , P. , Dannenberg , J. J. , Dapprich , S. , Daniels , A. D. , Farkas , Ö. , Foresman , J. B. , Ortiz , J. V. , Cioslowski , J. and Fox , J. D. 2009 . Gaussian 09, Revision A.02 Gaussian, Inc., Wallingford , CT
  • Lee , C. , Yang , W. and Parr , R. G. 1988 . Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density . Phys. Rev. B , 37 : 785 – 789 .
  • Becke , A. D. 1992 . Density-functional thermochemistry. I. The effect of the exchange-only gradient correction . J. Chem. Phys. , 96 : 2155 – 2160 .
  • Becke , A. D. 1992 . Density-functional thermochemistry. II. The effect of the Perdew–Wang generalized-gradient correlation correction . J. Chem. Phys. , 97 : 9173 – 9177 .
  • Becke , A. D. 1993 . Density-functional thermochemistry. III. The role of exact exchange . J. Chem. Phys. , 98 : 5648 – 5652 .
  • Barone , V. and Cossi , M. 1998 . Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model . J. Phys. Chem. A , 102 : 1995 – 2001 .
  • Cossi , M. , Rega , N. , Scalmani , G. and Barone , V. 2003 . Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model . J. Comput. Chem. , 24 : 669 – 681 .

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