Studies on stereospecific formation of P-chiral internucleotide linkage: Synthesis of all-Rp and all-Sp methylphosphonate pentanucleotide d(MMTrA(PMe)T(PMe)T(PMe)C(PMe)TAc) via grignard activated coupling

Antisense and Nucleic Acid Drug Development

Volumn 7, Issue 1, 1997, Pages 23-30

  Jaworska Maslanka, Maria M ^a   Kacperczyk, Wojciech ^a   Korczynski, Dariusz ^a   Lesnikowski, Zbigniew J ^a,b,c,d  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c ATLANTA VA MEDICAL CENTER   (United States)

^d POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; METHYLPHOSPHONATE PENTANUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL REACTION; DRUG STRUCTURE; ESTERIFICATION; HUMAN IMMUNODEFICIENCY VIRUS 1; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0030950235     PISSN: 10872906     EISSN: None     Source Type: Journal    
DOI: 10.1089/oli.1.1997.7.23     Document Type: Article

References (6)

1. AGRAWAL, S., ed. (1996). Antisense Therapeutics. (Humana Press, Totowa, NJ.)
2. AGRAWAL, S., ed. (1993). Methods in Molecular Biology. Protocols for Oligonucleotides and Analogs. Synthesis and Properties. (Humana Press, Totowa, NJ), vol. 20.
3. BENIMETSKAYA, L., TONKINSON, J.L., KOZIOLKIEWICZ, M., KARWOWSKI, B., GUGA, P., ZELTSER, R., STEC, W.J., and STEIN, C.A. (1995). Binding of phosphorothioate oligodeoxynucleotides to basic fibroblast growth factor, recombinant soluble CD4, laminin and fibronectin is P-chirality independent. Nucleic Acids Res. 23, 4495-4501.
4. BURGER, A., and DAWSON, N.D. (1951). The reaction of dialkyl chlorophosphates with arylmagnesium halides. J. Org. Chem. 16, 1250-1254.
5. CORMIER, J.F., and PANNUZIO, T. (1991). An improvement in the stereospecific synthesis of dinucleoside methylphosphonates. Tetrahedron Lett. 32, 7161-7164.
6. ZEMLICKA, J., CHLADEK, S., HALADOVA, Z., and RYCHLIK, J. (1969). Aminoacyl derivatives of nucleosides, nucleotides, and polynucleotides. VIII. Preparation of 2′(3′)-O-L-phenylalanyluridine, -cytidine, -adenosine, -inosine, -guanosine, and 3′-O-L-phenylalanyl-2′-deoxy-adenosine. Collection Czechoslov. Chem. Commun. 34, 3755-3768.