A Proposal for a New Stereochemical Notation for P-Chiral Nucleotide Analogues and Related Compounds

Abstract

A new stereochemical notation for P-chiral nucleotide analogues and related compounds is proposed. In this notation, the names of configurations, designated as D _P and L _P, are derived from a geometrical relationship, rather than from priority rules, of substituents at the phosphorus centre. This new stereochemical description offers clear advantages over the CIP R/S nomenclature, particularly when used for comparing the influence of absolute configuration at the phosphorus centre on physicochemical and biological properties of oligonucleotide analogues or in stereochemical correlation analysis of P-chiral nucleotide derivatives.

Keywords:

• Stereochemical Notation
• D _p/L _p
• P = Chiral
• Nucleotide Analogues

The financial support from the State Committee for Scientific Research, Republic of Poland, and the Swedish Research Council, is gratefully acknowledged.