Modular Strategy to Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

Donatien De Rochambeau, Yuanye Sun, Maciej Barlog, Hassan S. Bazzi, Hanadi F. Sleiman

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Sequence-defined polymers with customizable sequences, monodispersity, substantial length, and large chemical diversity are of great interest to mimic the efficiency and selectivity of biopolymers. We report an efficient, facile, and scalable synthetic route to introduce many chemical functionalities, such as amino acids and sugars in nucleic acids and sequence-controlled oligophosphodiesters. Through achiral tertiary amine molecules that are perfectly compatible with automated DNA synthesis, readily available amines or azides can be turned into phosphoramidites in two steps only. Individual attachment yields on nucleic acids and artificial oligophosphodiesters using automated solid-phase synthesis (SPS) were >90% in almost all cases. Using this method, multiple water-soluble sequence-defined oligomers bearing a range of functional groups in precise sequences could be synthesized and purified in high yields. The method described herein significantly expands the library of available functionalities for nucleic acids and sequence-controlled polymers.

Original languageEnglish
Pages (from-to)9774-9786
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number17
DOIs
Publication statusPublished - 7 Sep 2018

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Nucleic Acids
Polymers
Amines
DNA
Bearings (structural)
Amino Sugars
Solid-Phase Synthesis Techniques
Biopolymers
Azides
Oligomers
Functional groups
Libraries
Amino Acids
Molecules
Water
phosphoramidite

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Modular Strategy to Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers. / De Rochambeau, Donatien; Sun, Yuanye; Barlog, Maciej; Bazzi, Hassan S.; Sleiman, Hanadi F.

In: Journal of Organic Chemistry, Vol. 83, No. 17, 07.09.2018, p. 9774-9786.

Research output: Contribution to journalArticle

De Rochambeau, Donatien ; Sun, Yuanye ; Barlog, Maciej ; Bazzi, Hassan S. ; Sleiman, Hanadi F. / Modular Strategy to Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 17. pp. 9774-9786.
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