메뉴 건너뛰기




Volumn 18, Issue 11, 2013, Pages 14268-14284

Synthesis of DNA/RNA and their analogs via phosphoramidite and H-phosphonate chemistries

Author keywords

Boranealkylphosphines; Boranephosphonates; DNA; H phosphonates; Metallophosphonates; Phosphoramidites; RNA

Indexed keywords

DNA; ORGANOPHOSPHORUS COMPOUND; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDOUS ACID; RNA;

EID: 84888605243     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181114268     Document Type: Review
Times cited : (93)

References (49)
  • 1
    • 0017302121 scopus 로고
    • Synthesis of thymidine oligonucleotides by phosphite triester intermediates
    • Letsinger; R.L.; Lunsford, W.B. Synthesis of thymidine oligonucleotides by phosphite triester intermediates. J. Am. Chem. Soc. 1976, 98, 3655-3661.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 3655-3661
    • Letsinger, R.L.1    Lunsford, W.B.2
  • 2
    • 0001009950 scopus 로고
    • The synthesis of oligodeoxyprimidines on a polymer support
    • Matteucci, M.D.; Caruthers, M.H. The synthesis of oligodeoxyprimidines on a polymer support. Tetrahedron Lett. 1980, 21, 719-722.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 719-722
    • Matteucci, M.D.1    Caruthers, M.H.2
  • 3
    • 33845556076 scopus 로고
    • Studies on nucleotide chemistry iv: Synthesis of deoxyoligonucleotides on a polymer support
    • Matteucci, M.D.; Caruthers, M.H. Studies on nucleotide chemistry iv: Synthesis of deoxyoligonucleotides on a polymer support. J. Am. Chem. Soc. 1981, 103, 3185-3191.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3185-3191
    • Matteucci, M.D.1    Caruthers, M.H.2
  • 4
    • 0001612798 scopus 로고
    • Oligonucleotide synthesis on a polymer support 1,2
    • Letsinger, R.L.; Mahadevan, V. Oligonucleotide synthesis on a polymer support 1,2. J. Am. Chem. Soc. 1965, 87, 3526-3527.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 3526-3527
    • Letsinger, R.L.1    Mahadevan, V.2
  • 5
    • 0040534542 scopus 로고
    • Dialkylaminophosphines. IV. Additions and substitutions on tris(Dimethylamino)phosphine
    • Vetter, H.J.; Noeth, H. Dialkylaminophosphines. IV. Additions and substitutions on tris(Dimethylamino)phosphine. Chem. Ber. 1963, 96, 1308-1315.
    • (1963) Chem. Ber. , vol.96 , pp. 1308-1315
    • Vetter, H.J.1    Noeth, H.2
  • 6
    • 0346512797 scopus 로고
    • Addition reactions to Amides of Silicon, Phosphorus, Arsenic, and Sulfur
    • Oertel, G.; Malz, H.; Holtschmidt, H. Addition reactions to Amides of Silicon, Phosphorus, Arsenic, and Sulfur. Chem. Ber. 1964, 97, 891-902.
    • (1964) Chem. Ber. , vol.97 , pp. 891-902
    • Oertel, G.1    Malz, H.2    Holtschmidt, H.3
  • 7
    • 84888600939 scopus 로고
    • Acid catalysis of derivatives of trivalent phosphorus acids
    • Mir Publishers: Moscow, Russia
    • Batyeva, E.S.; Al'fonsov, V.A.; Pudovik, A.N. Acid catalysis of derivatives of trivalent phosphorus acids. In Chemistry of Organophosphorus Compounds; Mir Publishers: Moscow, Russia, 1989; pp. 68-92.
    • (1989) Chemistry of Organophosphorus Compounds , pp. 68-92
    • Batyeva, E.S.1    Al'fonsov, V.A.2    Pudovik, A.N.3
  • 8
    • 49149135789 scopus 로고
    • Studies on Nucleotide Chemistry V: Deoxynucleoside Phosphoramidites-A New Class of Key Intermediates for Deoxypolynucleotide Synthesis
    • Beaucage, S.L.; Caruthers, M.H. Studies on Nucleotide Chemistry V: Deoxynucleoside Phosphoramidites-A New Class of Key Intermediates for Deoxypolynucleotide Synthesis. Tetrahedron Lett. 1981, 22, 1859-1862.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 1859-1862
    • Beaucage, S.L.1    Caruthers, M.H.2
  • 9
    • 7144238770 scopus 로고
    • An investigation of several deoxynucleoside phosphoramidites useful for synthesizing deoxyoligonucleotides
    • McBride, L.J.; Caruthers, M.H. An investigation of several deoxynucleoside phosphoramidites useful for synthesizing deoxyoligonucleotides. Tetrahedron Lett. 1983, 24, 245-248.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 245-248
    • McBride, L.J.1    Caruthers, M.H.2
  • 10
    • 77952530236 scopus 로고    scopus 로고
    • Synthesis of high-quality libraries of long (150mer) oligonucleotides by a novel depurination controlled process
    • Leproust, E.M.; Peck, B.J.; Spirin, K.; McCuen, H.B.; Moore, B.; Nomsaraev, E.; Caruthers, M.H. Synthesis of high-quality libraries of long (150mer) oligonucleotides by a novel depurination controlled process. Nucleic Acids Res. 2010, 38, 2522-2540.
    • (2010) Nucleic Acids Res. , vol.38 , pp. 2522-2540
    • Leproust, E.M.1    Peck, B.J.2    Spirin, K.3    McCuen, H.B.4    Moore, B.5    Nomsaraev, E.6    Caruthers, M.H.7
  • 11
    • 0001687673 scopus 로고
    • β-Cyanoethyl N,N-dialkylamino/N-morpholinomonochloro phosphoamidites, new phosphitylating agents facilitating ease of deprotection and work-up of synthesized oligonucleotides
    • Sinha, N.D.; Biernat, J.; Köster, H. β-Cyanoethyl N,N-dialkylamino/N-morpholinomonochloro phosphoamidites, new phosphitylating agents facilitating ease of deprotection and work-up of synthesized oligonucleotides. Tetrahedron Lett. 1983, 24, 5843-5846.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5843-5846
    • Sinha, N.D.1    Biernat, J.2    Köster, H.3
  • 12
    • 0013029875 scopus 로고
    • Directed Arbuzov-type reactions of 2-cyano-1,1-dimethylethyl deoxynucleoside phosphites
    • Nielsen, J.; Caruthers, M.H. Directed Arbuzov-type reactions of 2-cyano-1,1-dimethylethyl deoxynucleoside phosphites. J. Am. Chem. Soc. 1988, 110, 6275-6276.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6275-6276
    • Nielsen, J.1    Caruthers, M.H.2
  • 13
    • 45949116807 scopus 로고
    • (2-Cyano-1,1- dimethylethoxy)bis(diethylamino)phosphine: A convenient reagent for the synthesis of DNA fragments
    • Marugg, J.E.; Burik, A.; van der Marel, G.A.; van Boom, J.H.; Nielsen, J.; Dahl, O. (2-Cyano-1,1- dimethylethoxy)bis(diethylamino)phosphine: A convenient reagent for the synthesis of DNA fragments. Recl. Trav. Chim. Pays-Bas 1987, 106, 72-76.
    • (1987) Recl. Trav. Chim. Pays-Bas , vol.106 , pp. 72-76
    • Marugg, J.E.1    Burik, A.2    Van Der Marel, G.A.3    Van Boom, J.H.4    Nielsen, J.5    Dahl, O.6
  • 14
    • 0002216788 scopus 로고
    • Nucleotides. Part XVI. Ribonucleoside-5[prime or minute] phosphites. A new method for the preparation of mixed secondary phosphites
    • Corby N.S.; Kenner, G.W.; Todd, A.R. 704. Nucleotides. Part XVI. Ribonucleoside-5[prime or minute] phosphites. A new method for the preparation of mixed secondary phosphites. J. Chem Soc. 1952, 3669-3675.
    • (1952) J. Chem Soc. , vol.704 , pp. 3669-3669
    • Corby, N.S.1    Kenner, G.W.2    Todd, A.R.3
  • 15
    • 37049053283 scopus 로고
    • Nucleotides. Part XLI. Mixed anhydrides as intermediates in the synthesis of dinucleoside phosphates
    • 644
    • Hall, R.H.; Todd, A.; Webb, R.F. 644. Nucleotides. Part XLI. Mixed anhydrides as intermediates in the synthesis of dinucleoside phosphates. J. Chem. Soc. 1957, 3291-3296.
    • (1957) J. Chem. Soc. , pp. 3291-3296
    • Hall, R.H.1    Todd, A.2    Webb, R.F.3
  • 16
    • 27844555547 scopus 로고
    • Synthesis of a Dithymidine Dinucleotide Containing a 3':5'- Internucleotide Linkage
    • Michelson, A.M.; Todd, A.R. Synthesis of a Dithymidine Dinucleotide Containing a 3':5'-Internucleotide Linkage. J. Chem. Soc. 1955, 2632-2638.
    • (1955) J. Chem. Soc. , pp. 2632-2638
    • Michelson, A.M.1    Todd, A.R.2
  • 17
    • 0001378571 scopus 로고
    • The synthesis of phosphite analogues of ribonucleotides
    • Ogilvie, K.K.; Nemer, M.J. The synthesis of phosphite analogues of ribonucleotides. Tetrahedron Lett. 1980, 21, 4145-4148.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 4145-4148
    • Ogilvie, K.K.1    Nemer, M.J.2
  • 18
    • 0001231603 scopus 로고
    • Acylphosphonates. 4 Synthesis of dithymidine phosphonate. A new method for generation of phosphonate function via aroylphosphonate intermediates
    • Kume, A.; Fujii, M.; Sekine, M.; Hata, T. Acylphosphonates. 4 Synthesis of dithymidine phosphonate. A new method for generation of phosphonate function via aroylphosphonate intermediates. J. Org. Chem. 1984, 49, 2139-2143.
    • (1984) J. Org. Chem. , vol.49 , pp. 2139-2143
    • Kume, A.1    Fujii, M.2    Sekine, M.3    Hata, T.4
  • 19
    • 0001538665 scopus 로고
    • Formation of internucleotidic bonds via phosphonate intermediates
    • Garegg, P.J.; Regberg,T.; Stawinski, J.; Stromberg, R. Formation of internucleotidic bonds via phosphonate intermediates. Chemica Scripta 1985, 25, 280-282.
    • (1985) Chemica Scripta , vol.25 , pp. 280-282
    • Garegg, P.J.1    Regbergt2    Stawinski, J.3    Stromberg, R.4
  • 20
    • 0000096955 scopus 로고
    • Nucleoside H-phosphonates: Valuable intermediates in the synthesis of deoxyoligonucleotides
    • Froehler, B.C.; Matteucci, M.D. Nucleoside H-phosphonates: Valuable intermediates in the synthesis of deoxyoligonucleotides. Tetrahedron Lett. 1986, 27, 469-472.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 469-472
    • Froehler, B.C.1    Matteucci, M.D.2
  • 21
    • 0023046847 scopus 로고
    • Synthesis of DNA via deoxynucleoside H-phosphonate intermediates
    • Froehler, B.C.; Ng, P.G.; Matteucci, M.D. Synthesis of DNA via deoxynucleoside H-phosphonate intermediates. Nucleic Acids Res. 1986, 14, 5399-5407.
    • (1986) Nucleic Acids Res. , vol.14 , pp. 5399-5407
    • Froehler, B.C.1    Ng, P.G.2    Matteucci, M.D.3
  • 22
    • 0000096953 scopus 로고
    • Nucleoside H-phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach
    • Garegg, P.J.; Lindh, I.; Regberg, T.; Stawinski, J.; Strömberg, R.; Henrichson, C. Nucleoside H-phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach. Tetrahedron Letters 1986, 27, 4051-4054.
    • (1986) Tetrahedron Letters , vol.27 , pp. 4051-4054
    • Garegg, P.J.1    Lindh, I.2    Regberg, T.3    Stawinski, J.4    Strömberg, R.5    Henrichson, C.6
  • 23
    • 0000096954 scopus 로고
    • Nucleoside H-phosphonates. IV. Automated solid phase synthesis of oligoribonucleotides by the hydrogenphosphonate approach
    • Garegg, P.J.; Lindh, I.; Regberg, T.; Stawinski, J.; Strömberg, R.; Henrichson, C. Nucleoside H-phosphonates. IV. Automated solid phase synthesis of oligoribonucleotides by the hydrogenphosphonate approach. Tetrahedron Lett. 1986, 27, 4055-4058.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4055-4058
    • Garegg, P.J.1    Lindh, I.2    Regberg, T.3    Stawinski, J.4    Strömberg, R.5    Henrichson, C.6
  • 24
    • 0024283331 scopus 로고
    • Phosphoramidate analogues of DNA: Synthesis and thermal stability of heteroduplexes
    • Froehler, B.; Ng, P.; Matteucci, M. Phosphoramidate analogues of DNA: Synthesis and thermal stability of heteroduplexes. Nucleic Acids Res. 1988, 16, 4831-4839.
    • (1988) Nucleic Acids Res. , vol.16 , pp. 4831-4839
    • Froehler, B.1    Ng, P.2    Matteucci, M.3
  • 25
    • 0025676557 scopus 로고
    • Efficient synthesis of oligoribonucleotide and its phosphorothioate analogue using H-phosphonate approach
    • Agrawal, S.; Tang, J.Y. Efficient synthesis of oligoribonucleotide and its phosphorothioate analogue using H-phosphonate approach. Tetrahedron Lett. 1990, 31, 7541-7544.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7541-7544
    • Agrawal, S.1    Tang, J.Y.2
  • 26
    • 0028221544 scopus 로고
    • Nucleoside H-phosphonates.14 Synthesis of nucleoside phosphoroselenoates and phosphorothioselenoates via stereospecific selenization of the corresponding H-phosphonate and H-phosphonothioate diesters with the aid of new seleniumtransfer reagent, 3H-1,2
    • Stawinski, J.; Thelin, M. Nucleoside H-phosphonates.14 Synthesis of nucleoside phosphoroselenoates and phosphorothioselenoates via stereospecific selenization of the corresponding H-phosphonate and H-phosphonothioate diesters with the aid of new seleniumtransfer reagent, 3H-1,2. J. Org. Chem. 1994, 59, 130-136.
    • (1994) J. Org. Chem. , vol.59 , pp. 130-136
    • Stawinski, J.1    Thelin, M.2
  • 27
    • 37149040117 scopus 로고    scopus 로고
    • H-Phosphonates: Versatile synthetic precursors to biologically active phosphorus compounds
    • Kraszewski, A.; Stawinski, J. H-Phosphonates: Versatile synthetic precursors to biologically active phosphorus compounds. Pure Appl. Chem. 2007, 79, 2217-2227.
    • (2007) Pure Appl. Chem. , vol.79 , pp. 2217-2227
    • Kraszewski, A.1    Stawinski, J.2
  • 28
    • 0026276490 scopus 로고
    • Studies on reaction conditions for ribonucleotide synthesis via the H-phosphonate approach
    • Stawinski, J.; Stromberg, R.; Westman, E. Studies on reaction conditions for ribonucleotide synthesis via the H-phosphonate approach. Nucleic Acids Symp Ser. 1991, 228.
    • (1991) Nucleic Acids Symp Ser. , pp. 228
    • Stawinski, J.1    Stromberg, R.2    Westman, E.3
  • 29
    • 0025647806 scopus 로고
    • Boron-containing nucleic acids.2 Synthesis of oligodeoxynucleoside boranophosphates
    • Sood, A.; Shaw, B.R.; Spielvogel, B.F. Boron-containing nucleic acids.2 Synthesis of oligodeoxynucleoside boranophosphates. J. Am. Chem. Soc. 1990, 112, 9000-9001.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9000-9001
    • Sood, A.1    Shaw, B.R.2    Spielvogel, B.F.3
  • 30
    • 36948998836 scopus 로고    scopus 로고
    • Nucleoside and oligonucleoside boranophosphates: Chemistry and properties
    • Li, P.; Sergueeva, Z.A.; Dobrikov, M.; Shaw, B.R. Nucleoside and oligonucleoside boranophosphates: Chemistry and properties. Chem. Rev. 2007, 107, 4746-4796.
    • (2007) Chem. Rev. , vol.107 , pp. 4746-4796
    • Li, P.1    Sergueeva, Z.A.2    Dobrikov, M.3    Shaw, B.R.4
  • 31
    • 79959506574 scopus 로고    scopus 로고
    • Solid-phase synthesis, Thermal denaturation studies, Nuclease resistance, and Cellular uptake of (Oligodeoxyribonucleoside)methylborane Phosphine-DNA chimeras
    • Krishna, H.; Caruthers, M.H. Solid-phase synthesis, Thermal denaturation studies, Nuclease resistance, and Cellular uptake of (Oligodeoxyribonucleoside) methylborane Phosphine-DNA chimeras. J. Am. Chem. Soc. 2011, 133, 9844-9854.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 9844-9854
    • Krishna, H.1    Caruthers, M.H.2
  • 32
    • 0013421604 scopus 로고
    • Transition Metal Labeling of Oligodeoxyribonucleotides: Synthesis and Characterization of (Pentacarbonyl)tungsten(0) Nucleoside Phosphites
    • Toma, J.M.D.R.; Bergstrom, D.E. Transition Metal Labeling of Oligodeoxyribonucleotides: Synthesis and Characterization of (Pentacarbonyl)tungsten(0) Nucleoside Phosphites. J. Org. Chem. 1994, 59, 2418-2422.
    • (1994) J. Org. Chem. , vol.59 , pp. 2418-2422
    • Toma, J.M.D.R.1    Bergstrom, D.E.2
  • 33
    • 67650086555 scopus 로고    scopus 로고
    • Synthesis of (pentacarbonyl)tungstate(-1) and (pentacarbonyl)molybdate(- 1) dinucleotides
    • Pav, O.; Caruthers, M.H. Synthesis of (pentacarbonyl)tungstate(-1) and (pentacarbonyl)molybdate(-1) dinucleotides. Tetrahedron Lett. 2009, 50, 5015-5017.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 5015-5017
    • Pav, O.1    Caruthers, M.H.2
  • 34
    • 26644470835 scopus 로고    scopus 로고
    • Incorporation of ribonucleoside 5'-(alpha-P-borano)triphosphates into a 20-mer RNA by T7 RNA polymerase
    • Wan, J.; Shaw, B.R. Incorporation of ribonucleoside 5'-(alpha-P-borano) triphosphates into a 20-mer RNA by T7 RNA polymerase. Nucleosides Nucleotides Nucleic Acids 2005, 24, 943-946.
    • (2005) Nucleosides Nucleotides Nucleic Acids , vol.24 , pp. 943-946
    • Wan, J.1    Shaw, B.R.2
  • 35
    • 0028847025 scopus 로고
    • Boron-containing oligodeoxyribonucleotide 14mer duplexes: Enzymatic synthesis and melting studies
    • Li, H.; Porter, K.; Huang, F.; Shaw, B.R. Boron-containing oligodeoxyribonucleotide 14mer duplexes: enzymatic synthesis and melting studies. Nucleic Acids Res. 1995, 23, 4495-4501.
    • (1995) Nucleic Acids Res. , vol.23 , pp. 4495-4501
    • Li, H.1    Porter, K.2    Huang, F.3    Shaw, B.R.4
  • 36
    • 0030842860 scopus 로고    scopus 로고
    • Direct PCR sequencing with boronated nucleotides
    • Porter, K.W.; Briley, J.D.; Shaw, B.R. Direct PCR sequencing with boronated nucleotides. Nucleic Acids Res. 1997, 25, 1611-1617.
    • (1997) Nucleic Acids Res. , vol.25 , pp. 1611-1617
    • Porter, K.W.1    Briley, J.D.2    Shaw, B.R.3
  • 37
    • 11344251096 scopus 로고    scopus 로고
    • Diastereomers of 5'-O-adenosyl 3'-O-uridyl Boranophosphate [Up(BH3)A]: Synthesis and Nuclease Resistant Property
    • Proceedings of Symposium on RNA Biology III: RNA, Tool and Target, Research Triangle Park, NC, USA; Oxford University Press: Oxford, UK
    • He, K.; Shaw, B.R. Diastereomers of 5'-O-adenosyl 3'-O-uridyl Boranophosphate [Up(BH3)A]: Synthesis and Nuclease Resistant Property. In Nucleic Acids Symposium Series No. 41, Proceedings of Symposium on RNA Biology III: RNA, Tool and Target, Research Triangle Park, NC, USA, 1999; Oxford University Press: Oxford, UK; pp. 99-100.
    • (1999) Nucleic Acids Symposium Series No. 41 , pp. 99-100
    • He, K.1    Shaw, B.R.2
  • 39
    • 0030861430 scopus 로고    scopus 로고
    • Synthesis and hybridization study of a boranophosphatelinked oligothymidine deoxynucleotide
    • Zhang, J.; Terhorst, T.; Matteucci, M.D. Synthesis and hybridization study of a boranophosphatelinked oligothymidine deoxynucleotide. Tetrahedron Lett. 1997, 38, 4957-4960.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4957-4960
    • Zhang, J.1    Terhorst, T.2    Matteucci, M.D.3
  • 40
    • 0032560927 scopus 로고    scopus 로고
    • H-Phosphonate approach for solid-phase synthesis of oligodeoxyribonucleoside boranophosphates and their characterization
    • Sergueev, D.S.; Shaw, B.R. H-Phosphonate approach for solid-phase synthesis of oligodeoxyribonucleoside boranophosphates and their characterization. J. Am. Chem. Soc. 1998, 120, 9417-9427.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9417-9427
    • Sergueev, D.S.1    Shaw, B.R.2
  • 41
    • 3543017923 scopus 로고    scopus 로고
    • A novel method for the synthesis of dinucleoside boranophosphates by a boranophosphotriester method
    • Shimizu, M.; Wada, T.; Oka,N.; Saigo, K. A novel method for the synthesis of dinucleoside boranophosphates by a boranophosphotriester method. J. Org. Chem. 2004, 69, 5261-5268.
    • (2004) J. Org. Chem. , vol.69 , pp. 5261-5268
    • Shimizu, M.1    Wada, T.2    Oka, N.3    Saigo, K.4
  • 42
    • 33646945291 scopus 로고    scopus 로고
    • Solid-phase synthesis of oligodeoxyribonucleoside boranophosphates by the boranophosphotriester method
    • Shimizu, M.; Saigo, K.; Wada, T. Solid-phase synthesis of oligodeoxyribonucleoside boranophosphates by the boranophosphotriester method. J. Org. Chem. 2006, 71, 4262-4269.
    • (2006) J. Org. Chem. , vol.71 , pp. 4262-4269
    • Shimizu, M.1    Saigo, K.2    Wada, T.3
  • 44
    • 84876700169 scopus 로고    scopus 로고
    • Silver nanoassemblies constructed from boranephosphonate DNA
    • Roy, S.; Olesiak, M.; Shang, S.; Caruthers, M.H. Silver nanoassemblies constructed from boranephosphonate DNA. J. Am. Chem. Soc. 2013, 135, 6234-6241.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 6234-6241
    • Roy, S.1    Olesiak, M.2    Shang, S.3    Caruthers, M.H.4
  • 45
    • 58249103029 scopus 로고    scopus 로고
    • Stereocontrolled solid-phase synthesis of oligonucleoside H-phosphonates by an oxazaphospholidine approach
    • Iwamoto, N.; Oka, N.; Sato, T.; Wada, T. Stereocontrolled solid-phase synthesis of oligonucleoside H-phosphonates by an oxazaphospholidine approach. Angew. Chem. Int. Ed. 2009, 48, 496-499.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 496-499
    • Iwamoto, N.1    Oka, N.2    Sato, T.3    Wada, T.4
  • 46
    • 8144226085 scopus 로고    scopus 로고
    • Boranophosphate salts as an excellent mimic of phosphate salts: Preparation, characterization, and properties
    • Nahum, V.; Fischer, B. Boranophosphate salts as an excellent mimic of phosphate salts: preparation, characterization, and properties. Eur. J. Inorg. Chem. 2004, 2004, 4124-4131.
    • (2004) Eur. J. Inorg. Chem. , vol.2004 , pp. 4124-4131
    • Nahum, V.1    Fischer, B.2
  • 47
    • 0000540256 scopus 로고
    • Ylides, phosphoniumno d Orbitals but Walsh Diagrams and Maybe Banana Bonds: Chemical bonding in phosphines, Phosphine oxides, and phosphonium ylides
    • Gilheany, D.G. Ylides, phosphoniumno d Orbitals but Walsh Diagrams and Maybe Banana Bonds: Chemical bonding in phosphines, Phosphine oxides, and phosphonium ylides. Chemical Rev. 1994, 94, 1339-1374.
    • (1994) Chemical Rev. , vol.94 , pp. 1339-1374
    • Gilheany . D, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.