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First Aldehyde‐Functionalized Poly(2‐oxazoline)s for Chemoselective Ligation
Author(s) -
Taubmann Christian,
Luxenhofer Robert,
Cesana Sonia,
Jordan Rainer
Publication year - 2005
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.200500059
Subject(s) - oxazoline , aldehyde , chemoselectivity , chemistry , ligation , polymer chemistry , combinatorial chemistry , organic chemistry , surgery , medicine , catalysis
Summary: A protected aldehyde‐functionalized 2‐oxazoline, 2‐[3‐(1,3)‐dioxolan‐2‐ylpropyl]‐2‐oxazoline ( DPOx ), was synthesized from commercially available compounds in high yields. The polymerization of DPOx with different initiators proceeds via a living ionic mechanism; thus, the polymers were of low polydispersity and the degree of polymerization could be precisely adjusted. Copolymerization with 2‐methyl‐2‐oxazoline gave water‐soluble statistical copolymers. Hydrolysis of the homo‐ and copolymers resulted in well‐defined, aldehyde‐bearing poly(2‐oxazoline)s. The aldehyde side functions reacted quantitatively with an amino‐oxy compound to form the corresponding oxime.