Nucleobases, 2 -deoxyribonucleoside synthesis

Biochemical Retrosynthesis of 2 -Deoxyribonucleosides from Glucose Acetaldehyde and a Nucleobase Three-Step Multi-Enzyme-Catalyzed Synthesis... 

One-Pot Multi-Step Enzymatic Synthesis of 2 -Deoxyribonucleoside from Glucose, Acetaldehyde and a Nucleobase... 

Hanson, A. A., Rogan, E. G., and Cavalieri, E. L. (1998). Synthesis of adducts formed by iodine oxidation of aromatic hydrocarbons in the presence of deoxyribonucleosides and nucleobases. Chem Res Toxicol 11, 1201-1208. 

Suau T, Alvaro G, Benaiges MD et al. (2006) Influence of secondary reactions on the synthetic efficiency of DHAP-aldolases. Biotechnol Bioeng 93 48-55 Takayama S, McGarvey GJ, Won CH (1997) Microbial aldolases and transketolases new biocatalytic approaches to simple and complex sugars. Ann Rev Microbiol 51 285-310 Tischer W, Ihlenfeldt HG, Barzu O et al. (2001) Enzymatic synthesis of deoxyribonucleosides from deoxyribose 1-phosphate and nucleobase. Int. Patent WO014566. 

In this chapter, the preparation of monochlorophosphoramidite and phosphorodiamidite derivatives and their application toward a general synthesis of deoxyribonucleoside phosphoramidites will be delineated from representative literature procedures. The synthetic protocols provided herein should allow the preparation of a myriad of deoxyribonucleoside phosphoramidite monomers having any modification of the following entities nucleobases, nucleobase-protecting... 

To facilitate the design of deoxyribonucleoside phosphoramidite analogs, information regarding the activation of deoxyribonucleoside phosphoramidites will be provided to emphasize the importance imparted by the steric bulk of the substituents attached to the phosphorus center and to specific nucleobases on the coupling rates. The capping and oxidation steps of the synthetic cycle will also be discussed in relation to the potential formation of side products during oligonucleotide synthesis. 

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