PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA. Issue 15 (1st August 2017)

• Record Type: Journal Article
• Authors: Sugiyama, Toru; Hasegawa, Genki; Niikura, Chie; Kuwata, Keiko; Imamura, Yasutada; Demizu, Yosuke; Kurihara, Masaaki; Kittaka, Atsushi
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 15(2017)
• Page Start: 3337
• Page End: 3341
• Publication Date: 2017-08-01
• Subjects: Bhoc benzhydryloxycarbonyl -- HBTU 1-[bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate 3-oxide -- PyAOP 7-azabenzotriazol-1-yl-N-oxy-tris(pyrrolidino)-phosphonium hexafluorophosphate; Peptide nucleic acid -- Strand invasion -- Pseudocomplementary -- Antigene; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.06.015
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies.