Synthesis of Oligodeoxynucleotides Containing Electrophilic Groups

Xi Lin; Jinsen Chen; Shahien Shahsavari; Nathanael Green; Deepti Goyal; Shiyue Fang

doi:10.1021/acs.orglett.6b01878

Synthesis of Oligodeoxynucleotides Containing Electrophilic Groups

Org Lett. 2016 Aug 5;18(15):3870-3. doi: 10.1021/acs.orglett.6b01878. Epub 2016 Jul 22.

Authors

Xi Lin¹, Jinsen Chen¹, Shahien Shahsavari¹, Nathanael Green¹, Deepti Goyal¹, Shiyue Fang¹

Affiliation

¹ Department of Chemistry, Michigan Technological University , 1400 Townsend Drive, Houghton, Michigan 49931, United States.

Abstract

By use of 1,3-dithian-2-yl-methoxycarbonyl (Dmoc) as a protecting group and linker for oligodeoxynucleotide (ODN) synthesis, deprotection and cleavage are achieved under non-nucleophilic oxidative conditions. The nucleophile-sensitive thioester and α-chloroacetyl groups are conveniently incorporated into ODN sequences. The technology could be universally useful for electrophilic ODN synthesis.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Molecular Conformation
Oligodeoxyribonucleotides / chemical synthesis*
Oligodeoxyribonucleotides / chemistry

Substances

Oligodeoxyribonucleotides

Grants and funding

R15 GM109288/GM/NIGMS NIH HHS/United States