24 W. G. OVEREND AND M. STAGEY 



The chromatographic behavior of ribose has been extensively studied 

 and, as stated, the technique of partition chromatography has been used 

 to identify the sugar, particularly when it is present in small quantities in 

 admixture with other substances. Partridge'^^ has reported Rf values for 

 D-ribose in a variety of solvent mixtures (see Table II) and has shown that 

 as little as 30 ng. of the sugar can be handled according to his procedure. 



Using a column of powdered cellulose, separation of D-ribose from a four- 

 component mixture containing also galactose, rhamnose and arabinose, 

 was achieved successfully by Jones et al}^- Working on a 100-500 mg. scale, 

 crystalline ribose was recovered from this mixture in 94 % yield. 



Kuhn'^^ has measured the infrared absorption of D-ribose from 8 to 15 

 microns. 



h. -Glycosides 



As mentioned previously, Winter^^ claimed to have evidence supporting the exis- 

 tence of two pentose derivatives in animal (i.e., goats) tissues (e.g., liver and muscle), 

 one of which was probably an alkyl(ethyl) D-riboside. Confirmation of the discovery 

 has not yet been reported. Winter considered the possibility that the ethyl riboside 

 might have arisen during the process of tissue extraction, but dismissed the idea, 

 since arabinose failed to yield a glycoside under the conditions used for the isolation. 

 In view of subsequent work by Barker'^^ this conclusion was not justified, since ribose 

 rapidly forms a methyl ribofuranoside whereaa methyl arabofuranoside forms more 

 slowly. ^'^ 



H-OH 



MeO MeO 

 XVIII 



COjMe 



I 

 H-C-OMe 



I 

 H-C-OMe 



I 

 H-C-OMe 



COjMe 

 XX 



1" S. M. Partridge, Nature 158, 270 (1946); Biochem. J. 42, 238 (1948). 



"2 L. Hough, J. K. N. Jones, and W. H. Wadman, Nature 162, 448 (1948); /. Chem. 



Soc. 1949, 2511. 

 "3 L. P. Kuhn, Anal. Chem. 22, 276 (1950). 

 "* G. R. Barker, J. Chem. Soc. 1948, 2035. 

 »"> Edna M. Montgomery and C. S. Hudson, J. Am. Chem. Soc. 59, 992 (1937). 



