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.

Monitoring the solid-phase synthesis of depsides and depsipeptides. A color test for hydroxyl groups linked to a resin.

Tetrahedron ◽  
1999 ◽  
Vol 55 (51) ◽  
pp. 14807-14812 ◽  
Author(s):  
Oliver Kuisle ◽  
Manuel Lolo ◽  
Emilio Quiñoá ◽  
Ricardo Riguera
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydroxyl Groups ◽  
Color Test ◽  
Phase Synthesis

scholarly journals A new solid-phase synthesis of oligoribonudeotides by the pbosphoro-p-anisidate method using tetrahydrofuranyl protection of 2'-hydroxyl groups

1987 ◽  
Vol 15 (9) ◽  
pp. 3761-3772 ◽  
Author(s):  
Shigenori Jwai ◽  
Emi Yamada ◽  
Miyuki Asaka ◽  
Yoji Hayase ◽  
Hideo Inoue ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydroxyl Groups ◽  
Phase Synthesis

Construction of a 2,6-Difunctionalized 2-Methyl-2H-1-benzopyran Library by Using a Solid-Phase Synthesis Protocol

2005 ◽  
Vol 70 (24) ◽  
pp. 10151-10154 ◽  
Author(s):  
Jong Yeon Hwang ◽  
Hyung-Sub Choi ◽  
Jin-soo Seo ◽  
Hyun Ju La ◽  
Dong-Soo Kim ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Synthesis Protocol

scholarly journals Acylation of Lignin with Different Acylating Agents by Mechanical Activation-Assisted Solid Phase Synthesis: Preparation and Properties

Polymers ◽  
2018 ◽  
Vol 10 (8) ◽  
pp. 907 ◽  
Author(s):  
Xiaohong Zhao ◽  
Yanjuan Zhang ◽  
Mei Yang ◽  
Zuqiang Huang ◽  
Huayu Hu ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Mechanical Activation ◽  
Chain Length ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Carbon Number ◽  
Carbon Chain Length ◽  
Hydroxyl Groups ◽  
Phase Synthesis ◽  
Cyclic Anhydrides

Acylated lignins with substituents consisting of different lengths of carbon chains were prepared by a mechanical activation-assisted solid phase synthesis (MASPS) technology with a customized stirring ball mill as a reactor. The structures and properties were analyzed by UV/Vis, FTIR, NMR, SEM, DSC, and TG. The results showed that the acylated lignins were successfully prepared with either non-cyclic or cyclic anhydrides as the acylating agents. Both aliphatic hydroxyl and phenolic hydroxyl groups of lignin reacted with non-cyclic anhydrides, and different reactivity of acylating agents resulted in different relative contents of phenolic and aliphatic substituents in the products. The reactivity of the cyclic anhydrides was weaker than that of the non-cyclic anhydrides, and the reactivity of the acylating agents decreased with increasing carbon chain length and unsaturated bonds of acyl groups. All of the acylated lignins except maleylated lignin had a lower glass transition temperature (Tg) than the original lignin. The acylated lignins prepared with non-cyclic anhydrides had better thermal stability than original lignin, and the thermal stability increased, but Tg decreased with an increasing chain length of the acyl groups. The acylated lignins prepared with cyclic anhydrides had higher a Tg than those with non-cyclic anhydrides with the same carbon number, and the thermal stability was not obviously improved.

A new colorimetric test for detection of hydroxyl groups in solid-phase synthesis

2007 ◽  
Vol 48 (12) ◽  
pp. 2075-2078 ◽  
Author(s):  
Shiro Komba ◽  
Sayoko Sasaki ◽  
Sachiko Machida
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydroxyl Groups ◽  
Phase Synthesis ◽  
Colorimetric Test

scholarly journals Parallel solid-phase synthesis of diaryltriazoles

2012 ◽  
Vol 8 ◽  
pp. 1027-1036 ◽  
Author(s):  
Matthias Wrobel ◽  
Jeffrey Aubé ◽  
Burkhard König
Keyword(s):  
Protein Interactions ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Alpha Helix ◽  
Protein Protein Interactions ◽  
Phase Synthesis ◽  
Wang Resin ◽  
Polymer Bead ◽  
Synthesis Protocol ◽  
Parallel Fashion

A series of substituted diaryltriazoles was prepared by a solid-phase-synthesis protocol using a modified Wang resin. The copper(I)- or ruthenium(II)-catalyzed 1,3-cycloaddition on the polymer bead allowed a rapid synthesis of the target compounds in a parallel fashion with in many cases good to excellent yields. Substituted diaryltriazoles resemble a molecular structure similar to established terphenyl-alpha-helix peptide mimics and have therefore the potential to act as selective inhibitors for protein–protein interactions.

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