Solid-Phase Synthesis of DNA Chemical Sensor

2013 ◽  
Vol 815 ◽  
pp. 305-311 ◽  
Author(s):  
Hui Yong Zhang

Oligonucleotides are essential components of many applications in molecular biology. The synthesis chemistry is robust and commercial oligonucleotide synthesizers have taken advantage of the chemistry to provide oligonucleotides of high quality and purity. This paper established nucleic acid synthesis platform to carry out the synthesis of the labeled nucleic acid probes based on the DNA synthesizer and solid-phase synthesis technology. We chose to study the automated synthesis starting from DMT protected FAM labeled amidite attached to controlled pore glass (CPG) support and the standard trityl-off oligonucleotide synthesis cycle was performed, yielding the solid-supported oligonucleotide. The reported automated solid-phase oligonucleotide synthesis procedure successfully employs the common iterative synthesis, deblocking, activation, coupling, capping, oxidation, and isolation steps in standard oligonucleotide synthesis. The automated synthetic approach can also be applied to oligonucleotides of different length, composition of nucleotide, demonstrating the universality of the method. Moreover, the synthesis involved the use of commercially available, safe, stable, and inexpensive reagents, particularly advantageous and attractive for their use in automated solid-phase synthesis. The synthesis allows custom tailoring of their structure to the requirements of biological assays within hours, as opposed to traditional approaches that require weeks or months of work in the laboratory. Therefore it will become much easier to investigate biological interactions and optimize for objectives such as the receptor mediated targeting of oligonucleotides.

2012 ◽  
Vol 65 (5) ◽  
pp. 539 ◽  
Author(s):  
Elisse C. Browne ◽  
Steven J. Langford ◽  
Belinda M. Abbott

A convenient and cost-effective method for the synthesis of Fmoc/Boc-protected peptide nucleic acid monomers is described. The Fmoc/Boc strategy was developed in order to eliminate the solubility issues during peptide nucleic acid solid-phase synthesis, in particular that of the cytosine monomer, that occurred when using the commercialized Bhoc chemistry approach.


1995 ◽  
Vol 50 (7) ◽  
pp. 1096-1100 ◽  
Author(s):  
Ernst Bayer ◽  
Konrad Bleicher ◽  
Martin Maier

Polystyrene-polyethylene glycol (PS-PEG) tentacle polymers with loadings of up to 60/<μmol/g were used for standard oligonucleotide synthesis. As these resins are easy to handle and stable under reaction and cleavage conditions they may be used alternatively to controlled pore glass (CPG) as the most commonly used solid support for oligonucleotide synthesis. However, structural and chemical properties of the PS-PEG resins require modified conditions to guarantee syntheses with high coupling efficiencies. Oligonucleotides (ODN ) of various sequences and lengths have successfully been synthesized using HPLC and capillary electrophoresis (CE) for purity control. Additionally, electrospray mass spectrometry (ES-MS) was used for product identification.


2011 ◽  
Vol 47 (48) ◽  
pp. 12774 ◽  
Author(s):  
Aleksandra Liberska ◽  
Annamaria Lilienkampf ◽  
Asier Unciti-Broceta ◽  
Mark Bradley

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 7012
Author(s):  
Robert Wodtke ◽  
Jens Pietzsch ◽  
Reik Löser

Polyamines are highly attractive vectors for tumor targeting, particularly with regards to the development of radiolabeled probes for imaging by positron emission (PET) and single-photon emission computed tomography (SPECT). However, the synthesis of selectively functionalized derivatives remains challenging due to the presence of multiple amino groups of similar reactivity. In this work, we established a synthetic methodology for the selective mono-fluorobenz(o)ylation of various biogenic diamines and polyamines as lead compounds for the perspective development of substrate-based radiotracers for targeting polyamine-specific membrane transporters and enzymes such as transglutaminases. For this purpose, the polyamine scaffold was constructed by solid-phase synthesis of the corresponding oxopolyamines and subsequent reduction with BH3/THF. Primary and secondary amino groups were selectively protected using Dde and Boc as protecting groups, respectively, in orientation to previously reported procedures, which enabled the selective introduction of the reporter groups. For example, N1-FBz-spermidine, N4-FBz-spermidine, N8-FBz-spermidine, and N1-FBz-spermine and N4-FBz-spermine (FBz = 4-fluorobenzoyl) were obtained in good yields by this approach. The advantages and disadvantages of this synthetic approach are discussed in detail and its suitability for radiolabeling was demonstrated for the solid-phase synthesis of N1-[18F]FBz-cadaverine.


2016 ◽  
Vol 45 (5) ◽  
pp. 2116-2123 ◽  
Author(s):  
Frank J. L. Heutz ◽  
Paul C. J. Kamer

A highly modular solid-phase synthetic approach is presented which provides facile access to libraries of recyclable phosphine–phosphite ligands in quantitative yield requiring only minimal work-up.


1996 ◽  
Vol 24 (2) ◽  
pp. 201-206 ◽  
Author(s):  
Vibhakar J. Shah ◽  
Robert Cerpa ◽  
Irwin D. Kuntz, Jr. ◽  
George L. Kenyon

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