Linear oligosulfoxides: Synthesis and solubility studies

Halami, Bhaskar; Eriyagama, Dhananjani; Chillar, Komal; Nelson, Zack; Prehoda, Lucas; Yin, Yipeng; Lu, Bao-Yuan; Otto, Brett; Haggerty, Liam; Fang, Shiyue

doi:10.1016/j.tetlet.2019.151306

Cited by 4 publications

(4 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We thought that this compound would be highly soluble in water. To our surprise, it had very limited solubility in any solvents including water …”

Section: Results and Discussioncontrasting

confidence: 98%

“…To our surprise, it had very limited solubility in any solvents including water. 27 During the development of the technology, we found that using the trityl group instead of the DMTr group as the 5′-tag to assist RP HPLC purification was needed. When the DMTr group was used, the tag was unstable in the sodium periodate oxidation step.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups

et al. 2019

Self Cite

View full text Add to dashboard Cite

In traditional oligodeoxynucleotide (ODN) synthesis, phosphate groups are protected with the 2-cyanoethyl group, and amino groups are protected with acyl groups. At the end of ODN synthesis, deprotection is achieved with strong bases and nucleophiles. Therefore, traditional technologies are not suitable for the synthesis of ODNs containing sensitive functionalities. To address the problem, we report the use of Dim and Dmoc groups, which are based on the 1,3-dithian-2-yl-methyl function, for phosphate and amine protection for the solid phase ODN synthesis. Using the new Dim–Dmoc protection, deprotection was achieved under mild oxidative conditions without using any strong bases and nucleophiles. As a result, the new technology is suitable for the synthesis of ODNs containing sensitive functions. To demonstrate feasibility, seven 20-mer ODNs including four that contain sensitive ester and alkyl chloride groups were synthesized, purified with RP HPLC, and characterized with MALDI-TOF MS and enzyme digestion essays. High purity ODNs were obtained.

show abstract

“…We thought that this compound would be highly soluble in water. To our surprise, it had very limited solubility in any solvents including water …”

Section: Results and Discussioncontrasting

confidence: 98%

Section: ■ Results and Discussionmentioning

confidence: 99%

Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups

et al. 2019

Self Cite

View full text Add to dashboard Cite

show abstract

“…In an unrelated study, we found that even though DMSO is miscible with many solvents, the solubility of oligosulfoxides decreases rapidly as their lengths increase. 13 This prompted us to hypothesize that as ODNs grow, their solubility may decrease, and the reactions may become less efficient. Our success in the present study may inspire the use of PEGylation to improve the efficiency of unmodified DNA and RNA synthesis, which can have a high impact on projects in areas such as synthetic biology, 14 protein engineering, 15 mRNA vaccine development 16 and DNA computer digital data storage 17 in which the availability of long DNA and RNA is crucial for success.…”

Section: Resultsmentioning

confidence: 99%

PEGylated Dmoc phosphoramidites for sensitive oligodeoxynucleotide synthesis

Chillar,

Yin,

Apostle

et al. 2023

Org. Biomol. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…It is remarkable that the method has evolved to such a sophistication that the synthesis of (PEG) 16 was achieved in nine steps without any chromatography [18,27]. Besides PEGs, similar approaches have also been used for the synthesis of oligosulfoxides [28]. In this article, we report the use of monomers such as 2 containing a base-labile protecting group with the phenethyl group for stepwise monodisperse PEG synthesis.…”

Section: Introductionmentioning

confidence: 99%

Stepwise PEG synthesis featuring deprotection and coupling in one pot

D.¹,

Eriyagama²,

Yin³

et al. 2021

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

The stepwise synthesis of monodisperse polyethylene glycols (PEGs) and their derivatives usually involves using an acid-labile protecting group such as DMTr and coupling the two PEG moieties together under basic Williamson ether formation conditions. Using this approach, each elongation of PEG is achieved in three steps – deprotection, deprotonation and coupling – in two pots. Here, we report a more convenient approach for PEG synthesis featuring the use of a base-labile protecting group such as the phenethyl group. Using this approach, each elongation of PEG can be achieved in two steps – deprotection and coupling – in only one pot. The deprotonation step, and the isolation and purification of the intermediate product after deprotection using existing approaches are no longer needed when the one-pot approach is used. Because the stepwise PEG synthesis usually requires multiple PEG elongation cycles, the new PEG synthesis method is expected to significantly lower PEG synthesis cost.

show abstract

Linear oligosulfoxides: Synthesis and solubility studies

Cited by 4 publications

References 33 publications

Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups

Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups

PEGylated Dmoc phosphoramidites for sensitive oligodeoxynucleotide synthesis

Stepwise PEG synthesis featuring deprotection and coupling in one pot

Contact Info

Product

Resources

About