60 W. G. OVEREND AND M. STAGEY 



of barium hydroxide.^^^ The acid can be converted to a lactone: in solution 

 2-deoxy-L-ribonolactone undergoes no change in optical rotation during 

 8 days."^ Likewise 3 , 5-di-0-methyl-2-deoxy-L-ribonolactone underwent 

 neghgible hydrolysis, but 3,4-di-0-methyl-2-deoxy-L-ribonolactone was 

 completely hydrolyzed in 96 hours.^^^ When di-O-acetyl-D-arabinal is treated 

 with chlorine in chloroform solution, it yields 1 ,2-dichloro-l ,2-dideoxy-D- 

 pentose 3 , 4-di-O-acetate, which on reacting with silver carbonate in ether 

 is converted to 2-chloro-2-deoxypentose 3, 4-di-O-acetate. Heating with 

 lead oxide in a mixture of chloroform and water results in simultaneous re- 

 arrangement and deacetylation of the latter compound and affords 2-de- 

 oxy-D-ribonolactone .2'^ ^ 



Esters (e.g., 1,3,4-tri-O-acetate and 1,3,4-tri-O-benzoate) of 2-deoxy- 

 D-ribose have been obtained crystalline.^^^ The deoxypentose forms a ben- 

 2yi.278,279 ^j^fj p-nitrophenyl-hydrazone,"^ but does not form osazones. It 

 affords mercaptal derivatives,"^ and methyP*^ and trityP^^ ethers of the 

 sugar are also known. 



V. Addendum 



It has been demonstrated recently that D-ribose occurs in natural ma- 

 terials additional to those already described. A study of the immunologi- 

 cally active type-specific substance of Hemophilus influenzae, type b, has 

 given indications that this material consists of a polyribophosphate chain 

 as it exists in pentose nucleic acids, in which the place of the purines and 

 pyrimidines is occupied by a second similar chain, linked to the first in 

 1 , l'"-glycosidic linkages.*^* 



Several nucleosides and nucleotides have been isolated. Nebularine, 

 a natural product which was isolated*^^ from the mushroom, Agaricus 

 (Clitocybe) nehularis Batsch., and which gave purine and ribose on hy- 

 drolysis'^® has been shown to be 9-/3-D-ribofuranosylpurine.'" Marrian'^^ 

 claims to have a new adenine nucleotide which is adenosine-5'-tetraphos- 

 phate, and the isolation from yeast of a nucleotide containing both ribose 

 and mannose is reported. '^^ The properties of this latter nucleotide are 

 consistent with those of a structure in which the terminal phosphate group 

 of guanosine-5'-pyrophosphate is joined to a mannosyl residue, (i.e., it is 

 guanosine diphosphate mannose). 



^^* S. Zamenhof, Grace Leidy, Patricia L. Fitz Gerald, Hattie E. Alexander, and E. 



Chargaff, Federation Proc. 11, 315 (1952); /. Biol. Chem. 203, 695 (1953). 

 '1* L. Ehrenberg, H. Hedstrom, N. Lofgren, and B. Takman, Svensk. Kem. Tidskr 



58, 269 (1946). 

 3'« N. Lofgren, and B. Liining, Acta Chem. Scand. 7, 225 (1953). 

 "7 G. B. Brown and Virginia S. Weliky, /. Biol. Chem. 204, 1019 (1953). 

 "8 D. H. Marrian, Biochim. et Biophys. Acta 13, 278 (1954). 

 319 E. Cabib and L. F. Leloir, /. Biol. Chem. 206, 779 (1954). 



