Base-protected nucleotide analogs with protected thiol groups

Details Base-protected nucleotide analogs with protected thiol groups Base-protected nucleotide analogs with protected thiol groups

1997-07-23

1999-12-28

Marschel, Ardin H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

435 6, 436501, 536 231, 536 241, 536 243, 536 2431, 536 2432, 536 2433, 536 253, 935 77, 935 78, C07H 2100, C07H 2102, C07H 2104

Patent

active

060083344

ABSTRACT:
The present invention is directed to protected thiol analogs of pyrimidine bases for syntheses of DNA and RNA by chemical or enzymatic methods. The subject analogs include reagents suitable for DNA or RNA synthesis via phosphoramidite, H-phosphonate or phosphotriester chemistry as well a reagents suitable for use by RNA and DNA polymerase, including thermostable polymerases employed by PCR or other nucleic acid amplification techniques. The nucleotide analogs synthesized by methods of this invention can thus be incorporated into oligonucleotides or polynucleotides, deprotected and derivatized with a functional group. In some cases the protecting groups are themselves antigenic and may be left on the oligonucleotides or polynucleotides for detection with antibodies. A method of synthesizing oligonucleotides with a functional group using the subject nucleotide analogs is also provided.

REFERENCES:
patent: 4849513 (1989-07-01), Smith et al.
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PF Torrence et al.; "2'-Deoxy-5-(thiocyanato)uridine[1-(2-deoxy-=.beta.-D-crythropentofuranosy l)-5-(thiocyanato)uracil]: Direct Thiocyanation of a Pyrimidine Nucleoside"; Nucleic Acid Chem, ed. LB Townsend et al.; Abstract No. 90: 23559m; 1:367-370 (1978).
M. Hanna; "RNA Processing: Photoaffinity Cross-Linking Methods for Studying Protein Interactions", Methods in Enzymology, ed. James E. Dahlberg and John N. Abelson; Academic Press, Inc.; 180:383-405 (1989).
M. Hanna et al.; "Synthesis and Characterization of 5-[(4-Azidophenacyl)thio]uridine 5'-Triphosphate, a Cleavable Photo-Cross-Linking Nucleotide Analogue", Biochemistry, 28(14):5814-5820 (1989).
Bradley et al.; "Synthesis and Utility of 5-Thiocyanato Deoxyuridine and Uridine Phosphoramidites as Masked Synthons"; Tetrahedron Letters; 33(42):6223-6225 (1992).
M. Hanna et al.; "Synthesis and Characterization of a New Photocrosslinking CTP Analog and its Use on Photoaffinity labeling E. coli and T7 RNA Polymerases"; Nucleic Acids Research, 21(9):2073-2079 (1993).
He et al.; "Preparation of Probe-Modified RNA With 5-mercapto-UTP for Analysis of Protein-RNA Interactions"; Nucleic Acids Research; 23(7):1231-1238 (1995).
C.J. Welch et al.; "Synthesid of C-5 and N-3 Arenesulfenyl Uridines. Preparation and Properties of a New Class of Uracil Protecting Group"; Acta Chemica Scandinavica, B 39(1985) pp. 203-212. (1985).

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