Data storage in sequence-defined macromolecules via multicomponent reactions

Abstract Sequence-defined and information coding macromolecules suitable for data storage materials were synthesized via a combination of two multicomponent reactions. Thus, a well-established protocol based on the Passerini reaction was combined for the first time with the Biginelli reaction for monomer synthesis to explore new sequence-defined materials by exploiting the high structural variety of two multicomponent reactions. The information was encoded via the variation of six different components per repeating unit choosing from a list of more than 100 components that can potentially be applied. The structural variety of the oligomers that can achieved using this approach offers an information density of up to 24 bits per repeat unit. The information was read out via tandem mass spectrometry, wherein the predominant fragmentation processes were identified and subsequently applied for reading out the information contained within several macromolecules, i.e. by sequencing and re-establishing the structure of these macromolecules.

[1]  M. Meier,et al.  An Update on Isocyanide-Based Multicomponent Reactions in Polymer Science , 2017, Topics in Current Chemistry.

[2]  Jean-François Lutz,et al.  Coding Macromolecules: Inputting Information in Polymers Using Monomer-Based Alphabets , 2015 .

[3]  M. Meier,et al.  A Scalable and High-Yield Strategy for the Synthesis of Sequence-Defined Macromolecules. , 2016, Angewandte Chemie.

[4]  Jonathan L. Sessler,et al.  Encoding, Reading, and Transforming Information Using Multifluorescent Supramolecular Polymeric Hydrogels , 2018, Advanced materials.

[5]  Jean-François Lutz,et al.  Preparation of Information-Containing Macromolecules by Ligation of Dyad-Encoded Oligomers. , 2015, Chemistry.

[6]  G. Church,et al.  Next-Generation Digital Information Storage in DNA , 2012, Science.

[7]  John R. Yates,et al.  Peptide Sequencing by Tandem Mass Spectrometry , 2006 .

[8]  C. Kappe,et al.  Automated library generation using sequential microwave-assisted chemistry. Application toward the Biginelli multicomponent condensation. , 2001, Journal of combinatorial chemistry.

[9]  I. Ugi,et al.  Multicomponent Reactions with Isocyanides. , 2000, Angewandte Chemie.

[10]  Jean-François Lutz,et al.  MS/MS Digital Readout: Analysis of Binary Information Encoded in the Monomer Sequences of Poly(triazole amide)s. , 2016, Analytical chemistry.

[11]  Kuangsen Sung,et al.  Kinetics and mechanism of acid-catalyzed hydrolysis of cyclohexyl isocyanide and pKa determination of N-cyclohexylnitrilium ion , 2001 .

[12]  C. Barner‐Kowollik,et al.  A Combined Photochemical and Multicomponent Reaction Approach to Precision Oligomers. , 2018, Chemistry.

[13]  Jean-François Lutz,et al.  Design and synthesis of digitally encoded polymers that can be decoded and erased , 2015, Nature Communications.

[14]  Reza M Zadegan,et al.  Nucleic acid memory. , 2016, Nature materials.

[15]  Jean-François Lutz,et al.  Mass spectrometry sequencing of long digital polymers facilitated by programmed inter-byte fragmentation , 2017, Nature Communications.

[16]  M. Meier,et al.  Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction , 2015 .

[17]  M. Meier,et al.  Diversely Substituted Polyamides: Macromolecular Design Using the Ugi Four-Component Reaction , 2014 .

[18]  Yaniv Erlich,et al.  DNA Fountain enables a robust and efficient storage architecture , 2016, Science.

[19]  C. Kappe The Generation of Dihydropyrimidine Libraries Utilizing Biginelli Multicomponent Chemistry , 2003 .

[20]  Pavel Kratochvíl,et al.  Glossary of basic terms in polymer science (IUPAC Recommendations 1996) , 1996 .

[21]  M. Meier,et al.  Combining Two Methods of Sequence Definition in a Convergent Approach: Scalable Synthesis of Highly Defined and Multifunctionalized Macromolecules. , 2017, Chemistry.

[22]  Krzysztof Matyjaszewski,et al.  From precision polymers to complex materials and systems , 2016 .

[23]  Jean-François Lutz,et al.  Orthogonal Synthesis of "Easy-to-Read" Information-Containing Polymers Using Phosphoramidite and Radical Coupling Steps. , 2016, Journal of the American Chemical Society.

[24]  Paul R. McGonigal,et al.  Tunable solid-state fluorescent materials for supramolecular encryption , 2015, Nature Communications.

[25]  M. Meier,et al.  Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules. , 2017, Macromolecular rapid communications.

[26]  R. Aebersold,et al.  Analysis, statistical validation and dissemination of large-scale proteomics datasets generated by tandem MS. , 2004, Drug discovery today.

[27]  M. Mironov Design of Multi‐Component Reactions: From Libraries of Compounds to Libraries of Reactions , 2006 .

[28]  M. Meier,et al.  Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions , 2017, Beilstein journal of organic chemistry.

[29]  Ulrich S Schubert,et al.  "Polymeromics": Mass spectrometry based strategies in polymer science toward complete sequencing approaches: a review. , 2014, Analytica chimica acta.

[30]  Sang Joon Kim,et al.  A Mathematical Theory of Communication , 2006 .

[31]  Dennis Hofheinz,et al.  Multicomponent reactions provide key molecules for secret communication , 2018, Nature Communications.

[32]  Jean-François Lutz,et al.  Synthesis of molecularly encoded oligomers using a chemoselective "AB + CD" iterative approach. , 2014, Macromolecular rapid communications.

[33]  Christopher Barner-Kowollik,et al.  Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation , 2016, Nature Communications.

[34]  J. Lutz,et al.  Convergent synthesis of digitally-encoded poly(alkoxyamine amide)s. , 2015, Chemical Communications.