Abstract
The chemical synthesis of DNA and RNA is universally carried out using nucleoside phosphoramidites or H-phosphonates as synthons. This review focuses on the phosphorus chemistry behind these synthons and how it has been developed to generate procedures whereby yields per condensation approach 100% with very few side products. Additionally the synthesis and properties of certain DNA and RNA analogs that are modified at phosphorus will also be discussed. These analogs include boranephosphonates, metallophosphonates, and alkylboranephosphines.
Highlights
The ability to chemically synthesize 2'-deoxyoligonucleotides and oligoribonucleotides in high yield and purity has revolutionized biochemical research as well as enabled a large number of other technologies such as DNA/RNA based therapeutics, DNA forensics, and high-throughput sequencing
Phosphorus chemistry is central to the development of synthetic methods for preparing these important biological molecules and for achieving the high yield, high-throughput synthesis of oligonucleotides
Other Lewis acids can be used as demonstrated by the synthesis of dinucleotides containing a P (III) center complexed to pentacarbonyltungstate(-1) and pentacarbonylmolybdate(-1) (27) [32,33]
Summary
The ability to chemically synthesize 2'-deoxyoligonucleotides and oligoribonucleotides (oligonucleotides) in high yield and purity has revolutionized biochemical research as well as enabled a large number of other technologies such as DNA/RNA based therapeutics, DNA forensics, and high-throughput sequencing. The chemical structure of DNA/RNA consists of purines and pyrimidines attached to 2'-deoxyribose or ribose sugars These 2'-deoxyribonucleosides or ribonucleosides are joined via phosphodiester linkages. P (III) centers that enables the synthesis of DNA/RNA We will describe these developments by first reviewing the work of Robert Letsinger and co-workers as their research led to the phosphoramidite approach in our laboratory. P (III) chemistry for the synthesis of oligonucleotides Both approaches have been used to prepare a plethora of nucleic acid analogs modified at phosphorus. This is a vast field of research in itself and a comprehensive description of all the different derivatives is outside the scope of this review. We will instead discuss a recent and promising class of analogs in which a P (III) center is bonded to a Lewis acid such as borane and forms stable internucleotide linkages
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