Solid-Phase Synthesis of Deoxynucleic Guanidine (DNG) Oligomers and Melting Point and Circular Dichroism Analysis of Binding Fidelity of Octameric Thymidyl Oligomers with DNA Oligomers

1999 ◽  
Vol 121 (16) ◽  
pp. 3888-3896 ◽  
Author(s):  
Barry A. Linkletter ◽  
Istvan E. Szabo ◽  
Thomas C. Bruice
Keyword(s):  
Circular Dichroism ◽  
Melting Point ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Dna Oligomers ◽  
Phase Synthesis ◽  
Circular Dichroism Analysis ◽  
Circular Dichroïsm

scholarly journals Solid-Phase Synthesis and Circular Dichroism Study of β-ABpeptoids

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 178 ◽  
Author(s):  
Ganesh A. Sable ◽  
Kang Ju Lee ◽  
Hyun-Suk Lim
Keyword(s):  
Circular Dichroism ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Nmr Studies ◽  
Phase Synthesis ◽  
Methyl Group ◽  
Wide Range ◽  
Material Sciences ◽  
Folded Structures ◽  
Circular Dichroïsm

The development of peptidomimetic foldamers that can form well-defined folded structures is highly desirable yet challenging. We previously reported on α-ABpeptoids, oligomers of N-alkylated β2-homoalanines and found that due to the presence of chiral methyl groups at α-positions, α-ABpeptoids were shown to adopt folding conformations. Here, we report β-ABpeptoids having chiral methyl group at β-positions rather than α-positions as a different class of peptoids with backbone chirality. We developed a facile solid-phase synthetic route that enables the synthesis of β-ABpeptoid oligomers ranging from 2-mer to 8-mer in excellent yields. These oligomers were shown to adopt ordered folding conformations based on circular dichroism (CD) and NMR studies. Overall, these results suggest that β-ABpeptoids represent a novel class of peptidomimetic foldamers that will find a wide range of applications in biomedical and material sciences.

Acyclic analogs of nucleosides based on tris(hydroxymethyl)phosphine oxide: synthesis and incorporation into short DNA oligomers

2015 ◽  
Vol 21 (5) ◽  
pp. 303-314 ◽  
Author(s):  
Barbara Nawrot ◽  
Olga Michalak ◽  
Barbara Mikołajczyk ◽  
Wojciech J. Stec
Keyword(s):  
Phosphine Oxide ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydroxyl Groups ◽  
Dna Oligomers ◽  
Phase Synthesis ◽  
Complementary Dna ◽  
Dna Analogs ◽  
Dna Strands ◽  
Synthesis Protocol

AbstractTris-(hydroxymethyl)phosphine oxide (THPO) to a certain extent resembles a part of 2′-deoxyribofuranose, although it exists in an acyclic form only and the oxygen atom at the THPO phosphorus center provides additional hydration site or acceptor of hydrogen bonds. After proper protection of hydroxyl groups, THPO was functionalized with nucleobases and converted into phosphoramidite monomers suitable for incorporation into growing oligonucleotide chains within the solid phase synthesis protocol. The resultant THPO-DNA analogs show reduced affinity to complementary DNA strands, and are resistant towards snake venom and calf spleen exonucleases.

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