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Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach
Author(s) -
Trinh Thanh Tam,
Oswald Laurence,
ChanSeng Delphine,
Lutz JeanFrançois
Publication year - 2014
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201300774
Subject(s) - azide , monomer , chemistry , alkyne , dispersity , combinatorial chemistry , sequence (biology) , cycloaddition , click chemistry , polymer chemistry , stereochemistry , organic chemistry , polymer , biochemistry , catalysis
A library of eight sequence‐defined model oligomers, whose sequence is based on a (0,1) binary code, is prepared through chemoselective repeating cycles of amidification and copper‐assisted alkyne‐azide cycloaddition reactions from a non‐modified Wang resin. This library is constructed from two AB (A = acid, B = alkyne) building blocks, i.e., 4‐pentynoic acid and 2‐methyl‐4‐pentynoic acid acting, respectively, as non‐coding (0) and coding (1) monomer, and 1‐amino‐11‐azido‐3,6,9‐trioxaundecane as complementary CD (C = amine, D = azide) spacer building block. In particular, encoded triads are synthesized by consecutive covalent attachment of five building blocks (i.e., three coding/non‐coding monomers and two spacers). In this communication, optimal protocols for the synthesis of the targeted oligomers are reported along with their full characterization by 1 H NMR, MALDI‐TOF mass spectrometry, and size‐exclusion chromatography. It is found that all possible encoded triads (i.e., eight possibilities) could be synthesized using this approach. Indeed, monodisperse sequence‐defined oligomers are prepared and characterized in all cases.