A proposal for a new stereochemical notation for P-chiral nucleotide analogues and related compounds.
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.
Sobkowski
Michal
M
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan, Poland. msob@ibch.poznan.pl
Stawinski
Jacek
J
Kraszewski
Adam
A
D001671:Biochemistry / Q000379:methods; D015394:Molecular Structure; D009711:Nucleotides / Q000737:chemistry*; D013237:Stereoisomerism; D009626:Terminology as Topic
D009711:Nucleotides