Easily encodable/decodable digital polymers linked by dithiosuccinimide motif

Ding, Kunshan; Zhang, Yajie; Huang, Zhihao; Liu, Baolei; Shi, Qiunan; Hu, Lihua; Zhou, Nianchen; Zhang, Zhengbiao; Zhu, Xiulin

doi:10.1016/j.eurpolymj.2019.08.017

Cited by 24 publications

(16 citation statements)

References 54 publications

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“…As long as co‐monomers have different masses, reading such messages is a sequencing task as typically achieved in MS/MS, where the nature and relative location of building units can be retrieved by analyzing data with regard to specific fragmentation rules. This has been reported by most groups acting in the field for a variety of polymers such as poly(alkoxyamine amide)s, 4 poly(triazole amide)s, 5 polyurethanes, 6 poly(alkoxyamine phosphodiester)s, 7 poly(ester amide)s, 8 poly(urethane amide)s, 9 poly(succinimide thioester)s, 10,11 and polyesters 12 . As shown in all these studies using collisional activation, one primary requirement for reliable sequencing is the occurrence of backbone bond cleavages, independently of the sequence, in order to generate product ions that contain either one or the other original chain end.…”

Section: Introductionmentioning

confidence: 78%

Optimal conditions for tandem mass spectrometric sequencing of information‐containing nitrogen‐substituted polyurethanes

Charles

Mondal

Greff

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale To prevent solubility issues faced with sequence‐defined polyurethanes, a new family of digital polyurethanes was conceived with the alkyl coding chain held by the carbamate nitrogen (N) atom and CH3 instead of OH as the ϖ termination. This led to different dissociation mechanisms that were explored prior to optimizing tandem mass spectrometric (MS/MS) sequencing. Methods N‐Substituted polyurethanes (N–R PUs) were dissolved in methanol and subjected to collision‐induced dissociation (CID) as deprotonated chains in the negative ion mode, and as ammonium and sodium adducts in the positive ion mode, using electrospray ionization (ESI) as the ionization technique. Their dissociation behavior was thoroughly investigated using a quadrupole time‐of‐flight (QTOF) instrument in order to provide accurate mass measurements to support proposed fragmentation mechanisms. Results While O–(CO) bonds were broken in N–H PUs, the CH2–O linkage between repeating units was cleaved upon CID of N–R PUs. This main process occurred either from deprotonated molecules or from cationized chains but was followed by different rearrangements, producing up to four product ion series. Yet, MS/MS spectra could be drastically simplified for precursor ions having their acidic α group methylated, as was found to spontaneously occur upon storage in methanol. Conclusions Using experimental conditions aimed at avoiding any reactive proton in precursor ions (no acidic end‐groups and alkali adduction), full coverage sequence of N–R PUs was successfully achieved with the single ion series observed in MS/MS, opening a promising perspective for reading large amounts of information stored in these dyad‐encoded polymers.

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Section: Introductionmentioning

confidence: 78%

Optimal conditions for tandem mass spectrometric sequencing of information‐containing nitrogen‐substituted polyurethanes

Charles

Mondal

Greff

et al. 2020

Rapid Comm Mass Spectrometry

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“…For the latter two substance classes, decoding and imaging from a surface via DESI was shown recently 38 . Information-containing oligomers, obtained by a thia-maleimide Michael coupling and read-out using MALDI-TOF MS/MS, were reported by Zhang and coworkers 39 , 40 . Kéki focused on an alcohol-isocyanate click approach for the synthesis of encoded polyethylene glycol 41 .…”

Section: Introductionmentioning

confidence: 98%

Molecular data storage with zero synthetic effort and simple read-out

Bohn

Weisel

Wolfs

et al. 2022

Sci Rep

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Compound mixtures represent an alternative, additional approach to DNA and synthetic sequence-defined macromolecules in the field of non-conventional molecular data storage, which may be useful depending on the target application. Here, we report a fast and efficient method for information storage in molecular mixtures by the direct use of commercially available chemicals and thus, zero synthetic steps need to be performed. As a proof of principle, a binary coding language is used for encoding words in ASCII or black and white pixels of a bitmap. This way, we stored a 25 × 25-pixel QR code (625 bits) and a picture of the same size. Decoding of the written information is achieved via spectroscopic (1H NMR) or chromatographic (gas chromatography) analysis. In addition, for a faster and automated read-out of the data, we developed a decoding software, which also orders the data sets according to an internal “ordering” standard. Molecular keys or anticounterfeiting are possible areas of application for information-containing compound mixtures.

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“…[ 4–18 ] Inspired by this, chemists demonstrated sequence‐defined synthetic polymer can be used as an alternative data recorder, termed as digital polymer by Lutz et al [ 19–21 ] By employing two different monomers regarded as binary codes “0” and “1,” binary digital message can be encoded in the polymer chain through iterative synthetic strategies [ 22–35 ] and retrieved by tandem mass spectrometry (MS/MS) [ 36–46 ] as well as nanopore‐sequencing technique. [ 47,48 ] Compared to DNA, digital polymer displays higher chemical stability, better compatibility, and broader structural designability, [ 24,34,49,50 ] which improve the storage capacity [ 28,29,51–56 ] and facilitate decoding process [ 34,43,57–61 ] as well as applications. [ 44,53,62–66 ] While most of the efforts have been spent on novel structure and application design of digital polymers, few attentions were paid to implement the basic function of digital polymers, that is, designing a practical storing device or carrier of digital polymers for arbitrary writing and reading information in a reliable manner.…”

Section: Introductionmentioning

confidence: 99%

“…Our group has been focused on storing information in digital polymers based on various maleimide motifs since 2017, [34,35,53,57,67] including thiosuccinimide, dithiosuccinimide (DTS) and succinimide sulfoxide moieties, which are synthesized by a series of novel maleimide chemistry and significantly improve the readabilities of digital polymers. Moreover, we strongly believe that the ultimate application of the digital polymer is to create a device, which would be more practical and beneficial to data writing and reading.…”

Section: Introductionmentioning

confidence: 99%

Fabrication and Decryption of a Microarray of Digital Dithiosuccinimide Oligomers

Shi

Miao

Liu

et al. 2022

Macromol. Rapid Commun.

Self Cite

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Digital polymers with precisely arranged binary units provide an important option for information storage. This is especially true if the digital polymers are assembled in a device, as it would be of great benefit for data writing and reading in practice. Herein, inspired by the DNA microarray technique, the programmable information storing and reading on a mass spectrometry target plate is proposed. First, an array of 4‐bit sequence‐coded dithiosuccinimide oligomers is efficiently built through sequential thiol‐maleimide Michael couplings with good sequence readability by tandem mass spectrometry (MS/MS). Then, toward engineering microarrays for information storage, a programmed robotic arm is specifically designed for precisely loading sequence‐coded oligomers onto the target plate, and a decoding software is developed for efficient readout of the data from MS/MS sequencing. Notably, short sequence‐coded oligomer chains can be used to write long strings of information, and extra error‐correction codes are not required as usual due to the inherent concomitant fragmentation signals. Not only text but also bitimages can be automatically stored and decoded with excellent accuracy. This work provides a promising platform of digital polymers for programmable information storing and reading.

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Easily encodable/decodable digital polymers linked by dithiosuccinimide motif

Cited by 24 publications

References 54 publications

Optimal conditions for tandem mass spectrometric sequencing of information‐containing nitrogen‐substituted polyurethanes

Optimal conditions for tandem mass spectrometric sequencing of information‐containing nitrogen‐substituted polyurethanes

Molecular data storage with zero synthetic effort and simple read-out

Fabrication and Decryption of a Microarray of Digital Dithiosuccinimide Oligomers

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