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Clickable Nucleic Acids: Sequence‐Controlled Periodic Copolymer/Oligomer Synthesis by Orthogonal Thiol‐X Reactions
Author(s) -
Xi Weixian,
Pattanayak Sankha,
Wang Chen,
Fairbanks Benjamin,
Gong Tao,
Wagner Justine,
Kloxin Christopher J.,
Bowman Christopher N.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506711
Subject(s) - copolymer , monomer , oligomer , polymer , sequence (biology) , nucleic acid , polymer chemistry , nucleobase , polymerization , click chemistry , thiol , chemistry , materials science , combinatorial chemistry , organic chemistry , dna , biochemistry
Synthetic polymer approaches generally lack the ability to control the primary sequence, with sequence control referred to as the holy grail. Two click chemistry reactions were now combined to form nucleobase‐containing sequence‐controlled polymers in simple polymerization reactions. Two distinct approaches are used to form these click nucleic acid (CNA) polymers. These approaches employ thiol–ene and thiol‐Michael reactions to form homopolymers of a single nucleobase (e.g., poly(A) n ) or homopolymers of specific repeating nucleobase sequences (e.g., poly(ATC) n ). Furthermore, the incorporation of monofunctional thiol‐terminated polymers into the polymerization system enables the preparation of multiblock copolymers in a single reaction vessel; the length of the diblock copolymer can be tuned by the stoichiometric ratio and/or the monomer functionality. These polymers are also used for organogel formation where complementary CNA‐based polymers form reversible crosslinks.