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Expanding the Scope and Orthogonality of PNA Synthesis
Author(s) -
Pothukanuri Srinivasu,
Pianowski Zbigniew,
Winssinger Nicolas
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800141
Subject(s) - chemistry , nucleobase , nucleic acid , combinatorial chemistry , oligonucleotide , orthogonality , nitrogen atom , protecting group , cornerstone , stereochemistry , biochemistry , dna , organic chemistry , group (periodic table) , alkyl , geometry , mathematics , art , visual arts
Peptide nucleic acids (PNAs) hybridize to natural oligonucleotides according to Watson and Crick base‐pairing rules. The robustness of PNA oligomers and ease of synthesis have made them an attractive platform to encode small or macromolecules for microarraying purposes and other applications based on programmable self assembly. A cornerstone of these endeavors is the orthogonality of PNA synthesis with other chemistries. Herein, we present a thorough investigation of six types of protecting groups for the terminal nitrogen atom (Alloc, Teoc, 4‐N 3 Cbz, Fmoc, 4‐OTBSCbz, and Azoc) and five protecting groups on the nucleobases (Cl‐Bhoc, F‐Bhoc, Teoc, 4‐OMeCbz, and Boc). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)