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  • Design and synthesis of digitally encoded polymers that can be decoded and erased.

Design and synthesis of digitally encoded polymers that can be decoded and erased.

Nature communications (2015-05-27)
Raj Kumar Roy, Anna Meszynska, Chloé Laure, Laurence Charles, Claire Verchin, Jean-François Lutz
ABSTRACT

Biopolymers such as DNA store information in their chains using controlled sequences of monomers. Here we describe a non-natural information-containing macromolecule that can store and retrieve digital information. Monodisperse sequence-encoded poly(alkoxyamine amide)s were synthesized using an iterative strategy employing two chemoselective steps: the reaction of a primary amine with an acid anhydride and the radical coupling of a carbon-centred radical with a nitroxide. A binary code was implemented in the polymer chains using three monomers: one nitroxide spacer and two interchangeable anhydrides defined as 0-bit and 1-bit. This methodology allows encryption of any desired sequence in the chains. Moreover, the formed sequences are easy to decode using tandem mass spectrometry. Indeed, these polymers follow predictable fragmentation pathways that can be easily deciphered. Moreover, poly(alkoxyamine amide)s are thermolabile. Thus, the digital information encrypted in the chains can be erased by heating the polymers in the solid state or in solution.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tris[2-(dimethylamino)ethyl]amine, 97%
Sigma-Aldrich
Piperidine, ReagentPlus®, 99%
Sigma-Aldrich
Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Butylated hydroxytoluene, ≥99%, FCC, FG
Sigma-Aldrich
2-Bromo-2-methylpropionic acid, 98%
Sigma-Aldrich
Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Piperidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Chloroform-d, "100%", 99.95 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, anhydrous
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer
Dichloromethane, suitable for HPLC, ≥99.7%
Sigma-Aldrich
Dimethyl sulfoxide, BioUltra, for molecular biology, ≥99.5% (GC)
Sigma-Aldrich
Methyl 2-bromopropionate, 98%
Sigma-Aldrich
N,N-Diisopropylethylamine, ReagentPlus®, ≥99%
Sigma-Aldrich
N,N-Diisopropylethylamine, purified by redistillation, 99.5%
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2-Bromopropionic acid, 99%
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TEMPO, 98%
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N,N,N′,N′′,N′′-Pentamethyldiethylenetriamine, 99%
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Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer
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4-Amino-TEMPO, free radical, 97%
Sigma-Aldrich
Dimethyl sulfoxide, anhydrous, ≥99.9%
Sigma-Aldrich
8-Octanoyloxypyrene-1,3,6-trisulfonic acid trisodium salt, suitable for fluorescence, ≥90% (HPCE)