Convenient Solid‐Phase Synthesis of Ureido‐Pyrimidinone Modified Peptides

Dankers, Patricia Y. W.; Adams, P. J.; Löwik, Dennis W. P. M.; Hest, Jan C. M. van; Meijer, E. W.

doi:10.1002/ejoc.200700191

Cited by 27 publications

(17 citation statements)

References 32 publications

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“…Moreover, computed vibrational normal modes go hand in hand with the experimentally observed ones (Table 1). 32,47,50 The slight differences observed are predicted to be due to the removal of protecting groups and lack of a physical environment for the computed models. 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Computational Studies on Structural, Excitation, and Charge-Transfer Properties of Ureidopeptidomimetics

2016

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Peptides with ureido group enclosing backbones are considered peptidomimetics and are known for their higher stabilities, biocompatibilities, antibiotic, inhibitor, and charge-transduction activities. These peptidomimetics have some unique applications, which are quite different from those of natural peptides. Hence, it is imperative to appreciate their properties at a microscopic level. In this regard, this work outlines, in detail, the charge transfer (CT) properties, holemigration dynamics, and electronic structures of various experimentally comprehended ureidopeptidomimetic models using density functional theory (DFT). Time-dependent DFT and complete active space self-consistent field computations on basic models provide the necessary evidence for the viability of CT from the end enfolding the ureido group to the other end with a carboxylate entity. This donor-to-acceptor CT has been reflected in excitation studies, in which the higher intensity band corresponds to CT from the π orbital of the ureido group to the π* orbital of the carboxylate entity. Further, hole-migration studies have shown that charge can evolve from the ureido end, whereas the hole generated at the carboxylate end does not migrate. However, hole migration has been reported to occur from both ends (amino and carboxylate ends) in glycine oligopeptides, and our studies show that the ability to transfer and migrate charge can be tuned by modifying the donor and acceptor functional groups in both the neutral and cationic charge states. We have analyzed the possibility of hole migration following ionization using DFT-based wave-packet propagation and found its occurrence on a ∼2−5 fs time scale, which reflects the charge-transduction ability of peptidomimetics.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Computational Studies on Structural, Excitation, and Charge-Transfer Properties of Ureidopeptidomimetics

2016

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“…A convenient solidphase synthesis method was developed to functionalize peptide sequences with UPy-moieties on the solid support. 146 Two different methods were used to couple the UPy-unit to the peptide sequence: via the free N-terminal amine, or via an additionally incorporated lysine, with an orthogonal protection group, at the C-terminus resulting in a UPy-peptide with a free N-terminal amine. UPy-peptides with an N-terminal cysteine were used to successfully functionalize green fluorescent protein mutants with UPy-moieties using native chemical ligation (unpublished results).…”

Section: Supramolecular Biomaterialsmentioning

confidence: 99%

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Dankers

Meijer²

2007

Bulletin of the Chemical Society of Japan

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123

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Supramolecular chemistry is an exciting area of science that plays a central role in bringing different disciplines together, ranging from molecular medicine to nanotechnology. Materials science based on supramolecular interactions is an emerging field, which has made important steps forward in the past ten years. The self-assembly of small synthetic molecules into long-chain architectures gives rise to the careful design of supramolecular polymers or fibers based on highly directional, reversible, non-covalent interactions. Much afford is put into the development of supramolecular (polymeric) materials with true materials properties, both in solution and in the solid state. These supramolecular materials are beginning to reach the market in all kind of applications. The field of regenerative medicine in general and that of tissue engineering in particular is one of the most challenging areas in which supramolecular materials might have a high potential. In tissue engineering, the biological environment and the interactions of cells with the artificial biomaterial is of utmost importance for the functioning of the implant, i.e. the engineered tissue. Ideal biomaterials do not only have to fulfil the biomaterials trinity of tuneable mechanical properties, regulation of the degradability and the ease for bioactivity incorporation, but also have to mimic the natural environment where the materials are brought into. Therefore, a modular, self-assembly approach using several supramolecular building blocks is an exquisite way to produce such ''responsive'' biomaterials. It is proposed that the artificial materials described in this account have the same type of dynamic ability to adapt its biofunctionality as is so well known for the living cells in the host tissue. This account will highlight two systems, i.e. self-assembling oligopeptide fibers as pioneered by Stupp et al. and Zhang et al., and our hydrogen-bonded supramolecular polymers, to show the potential of a modular approach to dynamic biomaterials for tissue engineering.

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“…For example, Meijer and co-workers designed ureido-pyrimidinone (UPy)-functionalized polymers able to incorporate a variety of peptide ligands. 13,14 Backbone polymer networks of UPy-functionalized polyesters provided sites where UPy-functionalized peptides could dock via four precise hydrogen bonds. The usefulness of this approach lies in its simplicity, as one can envision a nearly endless combination of UPy-functionalized peptides immobilized simply by mixing them together and applying them to the polymer matrix.…”

Section: Modular Ligand Presentation In Self-assembled Biomaterialsmentioning

confidence: 99%

“…A variety of UPy-functionalized peptides have already been produced, demonstrating the potential breadth of this approach. 13 An analogous strategy has also been utilized to decorate collagen matrices with peptides able to co-assemble non-covalently into the collagen triple helix.15 Other recent advances in modular self-assemblies have sought not to decorate a base scaffold but to construct the entire material from self-assembling small molecular weight components. For example, Stupp and coworkers recently extended their previous work with peptide-amphiphile biomaterials [16][17][18] by investigating the assembly and bioactivity of new peptide-amphiphiles capable of presenting additional ligands such as biotin, 9,19 RGD, 20,21 and others.…”

Section: Modular Ligand Presentation In Self-assembled Biomaterialsmentioning

confidence: 99%

Modular self-assembling biomaterials for directing cellular responses

Collier

2008

Soft Matter

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Self-assembling biomaterials are promising as cell-interactive matrices because they can be constructed in a modular fashion, which enables the independent and simultaneous tuning of several of their physicochemical and biological properties. Such modularity facilitates the optimization of multi-component matrices for use in complex biological environments such as 3-D cell culture or scaffolds for regenerative medicine. This Highlight will discuss recent strategies for producing modular self-assembling biomaterials, with a particular focus on how ligand presentation and matrix mechanics can be controlled in modular ways. In addition, it will discuss key hurdles that remain for employing these materials as cell-interactive scaffolds in biomedical applications, particularly those that relate to how they may interface with the immune system.

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Convenient Solid‐Phase Synthesis of Ureido‐Pyrimidinone Modified Peptides

Cited by 27 publications

References 32 publications

Computational Studies on Structural, Excitation, and Charge-Transfer Properties of Ureidopeptidomimetics

Computational Studies on Structural, Excitation, and Charge-Transfer Properties of Ureidopeptidomimetics

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Modular self-assembling biomaterials for directing cellular responses

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