Learning from Peptides to Access Functional Precision Polymer Sequences

Functional precision polymers based on monodisperse oligo(N‐substituted acrylamide)s and oligo(2‐substituted‐α‐hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side‐chain functionality sequences of a peptide with well‐studied properties. The peptide...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 58; no. 31; pp. 10747 - 10751
Main Authors: Maron, Eva, Swisher, Jordan H., Haven, Joris J., Meyer, Tara Y., Junkers, Tanja, Börner, Hans G.
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 29.07.2019
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Acrylamide
Additives
Chemistry
Chemistry, Multidisciplinary
drug delivery system
Drug delivery systems
monodisperse polymers
Payloads
peptide PEG conjugates
Peptides
Physical Sciences
Polymers
precision polymers
Science & Technology
sequence design
Solubilization
Substitutes
ACRYLATE OLIGOMERS
peptide PEG conjugates
sequence design
precision polymers
SOLID-PHASE SYNTHESIS
MONODISPERSE
monodisperse polymers
BIOCOMBINATORIAL STRATEGY
COPOLYMERS
drug delivery system
NEXT-GENERATION
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary:Functional precision polymers based on monodisperse oligo(N‐substituted acrylamide)s and oligo(2‐substituted‐α‐hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side‐chain functionality sequences of a peptide with well‐studied properties. The peptide was previously selected to solubilize the photosensitizer meta‐tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27‐times faster initial drug release. Not lost in translation: A new strategy to guide sequence design for accessing functional precision polymers is described. The direct translation of side‐chain functionality sequences into nonpeptidic backbones leads to macromolecules that mimic or improve on the properties of the parent peptide. As an example, the approach was applied to a peptide‐based formulation additive to solubilize a photosensitizer drug.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201902217