CHAPTER 2 



Chemistry of Ribose and Deoxyribose 

 W. G. OVEREND AND M. STAGEY 



Page 



I. Introduction 9 



II. Occurrence of D-Ribose and 2-Deox3^-i)-ribose 11 



III. Chemistry of Ribose 16 



1. Preparation 16 



2. Identification and Estimation 20 



3. Properties and Derivatives 22 



a. Physical Properties 22 



b. 0-Glycosides 24 



c. A''-Glycosides 27 



d. Phosphates 33 



(1) Ribose-1 -phosphate 36 



(2) Ribose-2- and -3-phosphates 37 



(3j Ribose-5-phosphate 39 



(4) Other Pentose Phosphates 41 



e. Ethers, Esters, Acetals and Anhydrides 42 



(1) Ethers ,42 



(2) Esters 43 



(3) Acetals 46 



(4) Anhydrides 46 



f. Other Properties 47 



IV. Chemistry of 2-Deo.\yribose 48 



1. Preparation 48 



2. Identification 53 



3. Physical Properties 55 



4. Properties and Reactions of Derivatives 55 



a. 0-Glycosides 55 



b. iV-Glycosides 56 



c. Phosphates 58 



d. Other Derivatives and Reactions 59 



V. Addendum 60 



Appendix. Tables of Physical Constants of Derivatives 65 



I. Introduction 



In recent years knowledge of the chemistry of the sugar components of 

 nucleic acids has been considerably broadened. Methods have been de- 

 veloped for the synthesis of important derivatives of these sugars, and the 



