Acyclic Nucleoside Phosphonates Bearing (R)‐ or (S)‐9‐[3‐Hydroxy‐2‐(phosphonoethoxy)propyl] (HPEP) Moiety as Monomers for the Synthesis of Modified Oligonucleotides. Issue 37 (7th August 2018)

• Record Type: Journal Article
• Authors: Kaiser, Martin Maxmilian; Novák, Pavel; Rosenbergová, Šárka; Poštová‐Slavětínská, Lenka; Rosenberg, Ivan; Janeba, Zlatko
• Other Names: Hostomský Zdeněk guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 37(2018)
• Page Start: 5119
• Page End: 5126
• Publication Date: 2018-08-07
• Subjects: Nucleobases -- Oligonucleotides -- Nonamers -- Duplexes -- Hybridization -- Tm values; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800490
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Suitably protected ( R )‐ and ( S )‐HPEP {9‐[3‐hydroxy‐2‐(phosphonoethoxy)propyl]} derivatives containing adenine and thymine nucleobases were prepared as monomers for the introduction of acyclic nucleotide units into oligonucleotides. The solid phase synthesis of a series of ribo and 2′‐deoxyribo nonamers containing ( R )‐HPEP and ( S )‐HPEP units was successfully performed in both 5′ → 3′ and 3′ → 5′ directions. The measurement of thermal characteristics of the complexes of modified nonamers with complementary DNA and RNA strands revealed a general destabilizing effect of the introduced acyclic units on the thermal stability, but in several cases [ modif. RNA*RNA and modif. DNA*RNA with ( S )‐HPEPA units], the duplexes were characterized in terms of T m values. Abstract : A solid‐phase synthesis afforded a series of ribo and 2′‐deoxyribo nonamers containing acyclic nucleotide units. A general destabilizing effect of the introduced acyclic units on the thermal stability of complexes of modified nonamers with the complementary DNA and RNA strands was observed, but in cases with ( S )‐HPEPA units, the duplexes were characterized in terms of T m values.