CHEMISTRY OF KIBOSE AND DEOXYKIBOSE 61 



Wyatt and Coheu^^'' have demonstrated that deoxyribonucleic acids of 

 bacteriophages T2, T4, and T6 of Escherichia colt contain no cytosine: 

 instead the pyrimidine base, 5-hydroxymethylcytosine, is a component of 

 these nucleic acids. Subsequently, Weed and Courtenay^-' succeeded in 

 isolating a deoxyribonucleotide containing hydroxymethylcytosine from 

 the deoxyribonucleic acid of Escherichia coli bacteriophage. 



D-[l-C^'']-Ribose has been prepared.^- 2-Deoxy-D-ribose was obtained by 

 partial oxidation of 3-deoxy-D-glucose with sodium metaperiodate, fol- 

 lowed by deformylation of the product by rendering the reaction mixture 

 slightly alkaline. ^-^ The product was isolated as A^-phenyl-2-doxy-D-ribosyl- 

 amine. 



The synthesis of A^-(3,4-dimethylphenyl)-D-ribosylamine by a rearrange- 

 ment method has been reported.'^* 9-,S-D-Ribofuranosylpurine ("nebular- 

 ine") has been synthesized^" by condensation of the chloromercuri-deriva- 

 tive of purine and tri-O-acetyl-o-ribofuranosyl chloride according to the 

 general method of Davoll and Lowy.^" Alternatively, 6-chloro-9-i3-D-ribo- 

 furanosylpurine was prepared and subjected to reductive dehalogenation to 

 afford nebularine. Further syntheses of 5,G-dimethylbenzimidazole-a-D- 

 ribofuranoside (a-ribazole) have been reported. 2-Nitro-4,5-dimethyl-A''- 

 (2',3'-di-0-acetyl-5'-0-trityl-D-ribofuranosido)aniline was reduced to the 

 (iorresponding 2-amino derivative, and this syrupy product in benzene 

 solution was stirred with carbon disulfide and a base (i.e., barium hydrox- 

 ide) to afford 5,6-dimethyl-2-sulfhydrylbenzimidazole-2',3'-di-0-acetyl- 

 5'-0-trityl-D-ribofuranoside. Desulfurization with nickel of this latter 

 compound and removal of the acetyl and trityl residues gave 5 , 6-dimethyl- 

 benzimidazole-a-D-ribofuranoside (isolated as the picrate) but none of the 

 j8-isomer.'2® Condensation of 5,6-dimethylbenzimidazole in dry dioxane 

 at 100° with tri-0-acetyl-D-ribofuranosyl chloride followed by deacetylation 

 of the reaction product afforded 5,6-dimethylbenzimidazole-Q;- and -/3-ribo- 

 furanoside.^^^ The yields of products were 2% and 10%, respectively, based 

 on the amount of tetra-0-acetyl-D-ribofuranose used for prepg^ration of 

 the acetochloro-ribose. a-Ribazole phosphate has been synthesized by 

 phosphorylation of the 5'-0-trityl derivative of a-ribazole with either 



320 G. R. Wyatt and S. S. Cohen, Nahire 170, 1072 (1952); Ann. inst. Pasteur 84, 143 

 (1953) ; Biochem. J. 55, 774 (1953). 



321 L. L. Weed and T. A. Courtenay, J. Biol. Chem. 206, 735 (1954). 



522 Harriet L. Frush and H. S. Isbell, J. Research Natl. Bur. Standards 51, 307 (1953). 



323 P. A. J. Gorin and J. K. N. Jones, Nature 172, 1051 (1953). 



324 V. A. Konkova, Zhur. Obshchel Khim. 22, 1896 (1952). 



325 J. Davoll and B. A. Lowy, J. Am. Chem. Soc. 73, 1650 (1951). 



32« Dorothea Heyl, Edith C. Chase, C. H. Shunk, Marjorie U. Moore, Gladys A. 



Emerson, and K.'Folkers, J. Am. Chem. Soc. 76, 1355 (1954). 

 327 A. W. Johnson, G. W. Miller, J. A. Mills, and A. R. Todd, J. Chem.. Soc, 1963, 3061. 



