Nucleic acid related compounds. 35. Synthesis of 5-bromo- and 5-deuterio-3-deazauridine

1981 ◽  
Vol 59 (24) ◽  
pp. 3356-3359 ◽  
Author(s):  
Morris J. Robins ◽  
Chisato Kaneko ◽  
Masakatsu Kaneko
Keyword(s):  
Nucleic Acid ◽  
Anticancer Agent ◽  
Clinical Implications ◽  
Catalytic Hydrogenolysis ◽  
Related Compounds

Bromination of 3-deazauracil (4-hydroxy-2-pyridinone) (1) gave the 3,5-dibromo compound (2). Selective debromination of 2 gave 5-bromo-4-hydroxy-2-pyridinone (3). Trimethylsilylation of 3 and condensation of the product (4) in situ with tetra-O-acetyl-β-D-ribofuranose (5) using tin(IV) chloride as catalyst gave 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-bromo-4-hydroxy-2-pyridinone (7). Deprotection of 7 gave 5-bromo-3-deazauridine (6). Catalytic hydrogenolysis of 7 gave 3-deazauridine triacetate (8a) and deuteriolysis gave the 5-deuterio product (8b). Deprotection of 8b gave the isotope-labeled anticancer agent, 5-deuterio-3-deazauridine (9). Biochemical and clinical implications are discussed.

Nucleic acid related compounds. 36. Synthesis of the 2′-O-methyl and 3′-O-methyl ethers of guanosine and 2-aminoadenosine and correlation of O′-methylnucleoside 13C nmr spectral shifts

1981 ◽  
Vol 59 (24) ◽  
pp. 3360-3364 ◽  
Author(s):  
Morris J. Robins ◽  
Fritz Hansske ◽  
Salwa E. Bernier
Keyword(s):  
Nucleic Acid ◽  
13C Nmr ◽  
Chloride Dihydrate ◽  
Spectral Shifts ◽  
Nmr Data ◽  
Related Compounds ◽  
In Situ Replacement ◽  
Isomeric Methyl ◽  
C Nmr

A modified trimethylsilylation of guanosine (1) followed by in situ replacement of the 6-trimethylsilyloxy group with ammonia at 150 °C gave 2,6-diamino-9-β-D-ribofuranosylpurine (2) in 92% yield. Treatment of 2 with diazomethane in the presence of tin(II) chloride dihydrate gave the 2′-O-methyl (3) and 3′-O-methyl (4) ethers of 2 in 98% combined yield. The ratios of 3/4 could be varied from 51:47 to 34:64 by changing the amount of catalyst used. Treatment of 3 and 4 with adenosine deaminase resulted in clean conversion of these 2-aminoadenosine ethers to 2′-O-methylguanosine (5) and 3′-O-methylguanosine (6), respectively, in optimized yields of 40% and 54% overall from 1. The 13C nmr data for six ribonucleosides and their isomeric methyl ether derivatives have been correlated to provide a convenient method of identification.

High-resolution nucleic acid sequence mapping via in situ hybridization at the Electron Microscope level

1995 ◽  
Vol 53 ◽  
pp. 752-753
Author(s):  
B.A. Hamkalo ◽  
S. Narayanswami ◽  
A.P. Kausch
Keyword(s):  
Nucleic Acid ◽  
Interphase Nucleus ◽  
Genome Mapping ◽  
Precise Location ◽  
Electron Microscope Level ◽  
Rna Sequences ◽  
Fundamental Interest ◽  
Whole Cells ◽  
Dna And Rna

The availability of nonradioactive methods to label nucleic acids an the resultant rapid and greater sensitivity of detection has catapulted the technique of in situ hybridization to become the method of choice to locate of specific DNA and RNA sequences on chromosomes and in whole cells in cytological preparations in many areas of biology. It is being applied to problems of fundamental interest to basic cell and molecular biologists such as the organization of the interphase nucleus in the context of putative functional domains; it is making major contributions to genome mapping efforts; and it is being applied to the analysis of clinical specimens. Although fluorescence detection of nucleic acid hybrids is routinely used, certain questions require greater resolution. For example, very closely linked sequences may not be separable using fluorescence; the precise location of sequences with respect to chromosome structures may be below the resolution of light microscopy(LM); and the relative positions of sequences on very small chromosomes may not be feasible.

scholarly journals THE ASSIMILATION OF NUCLEIC ACID DERIVATIVES AND RELATED COMPOUNDS BY YEASTS

1951 ◽  
Vol 189 (1) ◽  
pp. 151-157 ◽  
Author(s):  
Frederick J. Di Carlo ◽  
Alfred S. Schultz ◽  
Doris K. McManus
Keyword(s):  
Nucleic Acid ◽  
Related Compounds

Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides

1983 ◽  
Vol 26 (5) ◽  
pp. 661-666 ◽  
Author(s):  
Erik De Clercq ◽  
Johan Descamps ◽  
Jan Balzarini ◽  
Jerzy Giziewicz ◽  
Philip J. Barr ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Biological Activities ◽  
Related Compounds

Intercalation of Anticancer Agent Cytarabine and Its Related Compounds intoγ-Titanium Phosphate

1997 ◽  
Vol 70 (12) ◽  
pp. 3011-3015 ◽  
Author(s):  
Mayumi Danjo ◽  
Yukari Mizuguchi ◽  
Yukari Yagita ◽  
Kazuyo Kakiguchi ◽  
Tomomi Yanagida ◽  
...  
Keyword(s):  
Anticancer Agent ◽  
Titanium Phosphate ◽  
Related Compounds

scholarly journals Locked Nucleic Acid In situ Hybridization Analysis of miR-21 Expression during Colorectal Cancer Development

2009 ◽  
Vol 15 (12) ◽  
pp. 4009-4016 ◽  
Author(s):  
Nobutake Yamamichi ◽  
Ryoichi Shimomura ◽  
Ken-ichi Inada ◽  
Kouhei Sakurai ◽  
Takeshi Haraguchi ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
In Situ Hybridization ◽  
Nucleic Acid ◽  
Hybridization Analysis ◽  
Locked Nucleic Acid ◽  
Cancer Development
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