Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Solleder, Susanne C.; Schneider, Rebekka V.; Wetzel, Katharina S.; Boukis, Andreas C.; Meier, Michael A. R.

doi:10.1002/marc.201600711

Cited by 180 publications

(178 citation statements)

References 184 publications

(531 reference statements)

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“…The synthetic approaches toward sequence-defined macromolecules were recently summarized and can generally be divided into liquid-phase approaches, solid-phase approaches, and fluorous-phase or polymer-tethered methodologies, [2] with all their individual advantages and disadvantages. The synthetic approaches toward sequence-defined macromolecules were recently summarized and can generally be divided into liquid-phase approaches, solid-phase approaches, and fluorous-phase or polymer-tethered methodologies, [2] with all their individual advantages and disadvantages.…”

Section: Synthetic Approachesmentioning

confidence: 99%

“…[2] For instance, monodisperse oligofluorenes were obtained in an IEG approach (refer to Figure 2) up to the 64-mer stage and their degree of polymerization was correlated to their solid-phase morphology. High degrees of polymerization in these stiff and conjugated molecules were already achieved.…”

Section: Sequence Leads To Properties and Materials Applications In Camentioning

confidence: 99%

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A New Class of Materials: Sequence‐Defined Macromolecules and Their Emerging Applications

2019

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Emerging applications of a new class of materials, sequence‐defined macromolecules, are explored. Such molecularly highly defined macromolecules require stringent synthesis and purification procedures, yet offer unprecedented application possibilities. The first examples of molecular data storage and related technologies are already starting to emerge today. From a more fundamental point of view, such macromolecules offer a unique opportunity to determine quantitative structure–property relationships (QSPR), which critically aids in designing materials with applications ranging from catalysis to artificial enzymes.

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Section: Synthetic Approachesmentioning

confidence: 99%

Section: Sequence Leads To Properties and Materials Applications In Camentioning

confidence: 99%

A New Class of Materials: Sequence‐Defined Macromolecules and Their Emerging Applications

2019

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“…More recently, an increasing attention has been focused on the precise control of the sequence of polymers. The preparation of sequence‐controlled polymers has been approached through various approaches based on kinetic considerations, catalysis, template chemistry, multicomponent reaction, (macro)molecular design, and iterative synthesis . While the control of the microstructure of polymers still remains a challenge for polymer chemists, the ability to tune the sequence of polymers would be an asset for applications in materials sciences.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Macromolecules Containing Phenylalanine and Aliphatic Building Blocks

Chan‐Seng

Louwsma

Lutz

et al. 2018

Macromol. Rapid Commun.

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Aiming at developing efficient interfacial agents for fiber-reinforced composite materials, macromolecules are designed to have different components able to stick to the fiber and be compatible with the polymer matrix, respectively. Herein, macromolecules are prepared by solid-phase synthesis considering phenylalanine residues to promote adsorption of the macromolecule on aramid fibers and aliphatic building blocks to interact with a hydrophobic polymer matrix. Using phenylalanine as building block for the preparation of macromolecules by iterative synthesis has been shown to be challenging. Thus, the screening of various parameters for the optimization of the synthesis of these macromolecules is discussed in this communication. A preliminary thermal study by thermal gravimetric analysis is conducted to evaluate their thermal stability.

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“…Repetitive coupling of the same building block achieves full conversion; however, this comes at the cost of excess nonconjugated building blocks which end up in the waste. [14][15][16][17] Indeed, several of these strategies rely on the use of solid phase synthesis and the assembly of tailor-made building blocks. per coupling and double couplings are performed, resulting in 40-180 eq.…”

mentioning

confidence: 99%

Recovery, Purification, and Reusability of Building Blocks for Solid Phase Synthesis

Shamout

Fischer

Snyder

et al. 2019

Macromol. Rapid Commun.

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reagents and protecting group strategies, solid phase approaches regularly rely on the use of a high excess of building blocks and reagents in every addition step. Repetitive coupling of the same building block achieves full conversion; however, this comes at the cost of excess nonconjugated building blocks which end up in the waste. For example, for the standard Fmoc peptide synthesis of a decamer, amino acids are used in 5-10 equivalents (eq.) per coupling and double couplings are performed, resulting in 40-180 eq. of amino acids that will end up in the solvent waste. While many building blocks for the synthesis of peptides and oligonucleotides are commercially available at low cost, other building blocks are rare or commercially more expensive. Examples of such building blocks include non-natural amino acids, 13 C-and 15 N-labeled amino acids, and glycan donors. [5,[8][9][10][11][12] For building blocks that have to be synthesized prior to SPS, for example, glycosylated building blocks or building blocks that are used in the SPS of synthetic polymers, the use of excess building blocks is a major limitation in terms of cost, time, and labor. [13] Within the last decade, polymer chemists have successfully developed advanced strategies to introduce monomer sequence-control into synthetic polymers giving access to materials with new properties and applications such as drug delivery and data storage. [14][15][16][17] Indeed, several of these strategies rely on the use of solid phase synthesis and the assembly of tailor-made building blocks. [18] For example, Lutz et al. reported a SPS strategy for monodisperse and sequenceencoded poly(alkoxyamine amides) that allow for the storing of information in single polymer chains. [19,20] In the previous work, we have introduced the SPS of glycooligoamides as mimetics of oligosaccharides and their use in antibacterial treatment. [21,22] Although macromolecules synthesized via SPS can be expected to be high value products to enter the market in smaller quantities compared to commodity polymers, finding ways to produce such materials at low cost and with resource efficiency might further strengthen their applicability.Here we present the recovery, purification, and reusability of building blocks used in the solid phase assembly of glycooligoamides. The process relies on simple and well-established methods such as precipitation and recrystallization, and does not require any special equipment or expertise. It can be integrated into a standard peptide synthesizer for automated synthesis and is suitable for chemically different building blocks, as demonstrated here for tailor-made dimer building blocks, Solid phase synthesis (SPS) is well established for the synthesis of biomacro molecules such as peptides, oligonucelotides, and oligosaccharides, and today is also used for the synthesis of synthetic macromolecules and poly mers. The key feature of this approach is the stepwise assembly of building blocks on solid support, enabling monodispersity and monomer sequence control. Howe...

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Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Cited by 180 publications

References 184 publications

A New Class of Materials: Sequence‐Defined Macromolecules and Their Emerging Applications

A New Class of Materials: Sequence‐Defined Macromolecules and Their Emerging Applications

Synthesis of Macromolecules Containing Phenylalanine and Aliphatic Building Blocks

Recovery, Purification, and Reusability of Building Blocks for Solid Phase Synthesis

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