Fluorogenic Peptide Sequences − Transformation of Short Peptides into Fluorophores under Ambient Photooxidative Conditions

Gl, Juskowiak; Sj, Stachel; Tivitmahaisoon, Parcharee; Dl, Van Vranken

doi:10.1021/ja0379971

Cited by 12 publications

(8 citation statements)

References 33 publications

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“…A fluorescent hexapeptide was also demonstrated based on a prior work which studied the formation of a blue-emitting fluorophores as a result of photooxidation of specific tryptophan-containing peptides [ 25 ]. The hexapeptide was synthesized and oxidized under light in 2% hydrogen peroxide to produce a blue solution ( Fig 6A and 6B ).…”

Section: Resultsmentioning

confidence: 99%

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Design and validation of a frugal, automated, solid-phase peptide synthesizer

2020

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Solid phase peptide synthesis (SPPS) has enabled widespread use of synthetic peptides in applications ranging from pharmaceuticals to materials science. The demand for synthetic peptides has driven recent efforts to produce automated SPPS synthesizers which utilize fluid-handling components common to chemistry laboratories to drive costs down to several thousand dollars. Herein, we describe the design and validation of a more ‘frugal’ SPPS synthesizer that uses inexpensive, consumer-grade fluid-handling components to achieve a prototype price point between US$300 and $600. We demonstrated functionality by preparing and characterizing peptides with a variety of distinct properties including binding functionality, nanoscale self-assembly, and oxidation-induced fluorescence. This system yielded micromoles of peptide at a cost of approximately $1/residue, a cost which may be further reduced by optimization and bulk purchasing.

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Section: Resultsmentioning

confidence: 99%

“…containing peptides [25]. The hexapeptide was synthesized and oxidized under light in 2% hydrogen peroxide to produce a blue solution (Fig 6A and 6B).…”

Section: Plos Onementioning

confidence: 99%

Design and validation of a frugal, automated, solid-phase peptide synthesizer

2020

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Section: Characterization Of Fluorescent Peptidementioning

confidence: 99%

Design and Validation of a Frugal, Automated, Solid-Phase Peptide Synthesizer

Kallmyer

Rider

Reuel

2020

Preprint

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Solid phase peptide synthesis (SPPS) has enabled widespread use of synthetic peptides in applications ranging from pharmaceuticals to materials science. The demand for synthetic peptides has driven recent efforts to produce automated SPPS synthesizers which utilize fluidhandling components common to chemistry laboratories to drive costs down to several thousand dollars. Herein, we describe the design and validation of a more 'frugal' SPPS synthesizer that uses inexpensive, consumer-grade fluid-handling components to achieve a prototype price point between US$300 and $600. We demonstrated functionality by preparing and characterizing peptides with a variety of distinct properties including binding functionality, nanoscale selfassembly, and oxidation-induced fluorescence. This system yielded micromoles of peptide at a cost of approximately $1/residue, a cost which may be further reduced by optimization and bulk purchasing.

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“…This justifies the search for simpler peptide sequences that can give rise to self-assembling and self-catalyzing reactions leading to formation of fluorescent species. The focused search within constructed ~500,000-member solid-phase combinatorial library of Trp-containing Ala-flanked peptide hexamers led to successful findings that several non-fluorescent peptides selected from the library after UV irradiation and oxidation in the air attain intensive visible fluorescence (Juskowiak et al 2004). A number of analogs of GFP fluorophore have been synthesized (Ivashkin et al 2009).…”

Section: Finding Analogs Of Fluorescent Protein Fluorophoresmentioning

confidence: 99%

Molecular-Size Fluorescence Emitters

Demchenko

2015

Introduction to Fluorescence Sensing

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A variety of fluorescent and luminescent materials in the form of molecules, their complexes and nanoparticles are available for implementation as response units into sensing and imaging technologies and we discuss their general properties that are essential for these applications. Organic dyes were the first and remain to be the most popular emitters used with these purposes. Their labeling and responsive properties are overviewed. Natural fluorescent proteins and their engineered analogues incorporate organic fluorophores that are synthesized spontaneously from the polypeptide chain inside the living cells without the need of their intrusion, as the gene products. They resulted in revolutionary advancement in cell imaging and show good prospects in sensing and reporting on cellular processes. Organic heterocyclic compounds can incorporate metal ions generating long-living luminescence. Moreover, noble metal particles of a very small size exhibit unique light-absorbing and fluorescent emission properties. In this Chapter we focus on these types of fluorophores that possess subnanometer dimensions and display single type of absorption-emission cycle. The more complex nanostructures and nanocomposites will be overviewed in Chaps. 5 and 6 that follow. Fluorophores and Their Characteristics General Properties of Fluorescent DyesIn view of tremendous diversity of structures, chemical reactivities and spectroscopic properties, one needs certain practically useful criteria for the dye selection for the purpose of sensing and imaging. They can be formulated in the form of spectroscopic parameters that have to be optimized. It is the parameter describing the ability of molecule to absorb light at a particular wavelength. The absorbance E measured at any wavelength on spectrophotometer is proportional to the dye concentration c (in mol/l) and the light path length in a sample l (in cm). In this relation, ε plays the role of coefficient of proportionality, so that E = εcl. The value of molar absorbance is obtained by purifying and drying the dye, dissolving it at low concentration and measuring E on a spectrophotometer. The broadly used term extinction includes absorbance and light scattering. Absorbance is a unique characteristic of a molecule under certain environmental conditions. In general, the bigger the fluorophore size, the greater is the probability that the photon will be absorbed.The value of ε max at the maximum of absorption band is the common characteristic of the light-absorbing power of the dye. The dye 'brightness' that determines the absolute sensitivity of fluorescence detection (Wetzl et al. 2003) is the product of molar absorbance and quantum yield, Φ. The absorbance is related to optical cross-section and for organic dyes, ε max varies from ca. 10 3 l mol −1 cm −1 for small dyes, such as coumarins to ca. 10 5 l mol −1 cm −1 for larger fluorophores such as cyanines and phthalocyanines (Lavis and Raines 2008). It should be selected as high as possible, but the limiting factor is the fluorophore size. Us...

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Fluorogenic Peptide Sequences − Transformation of Short Peptides into Fluorophores under Ambient Photooxidative Conditions

Cited by 12 publications

References 33 publications

Design and validation of a frugal, automated, solid-phase peptide synthesizer

Design and validation of a frugal, automated, solid-phase peptide synthesizer

Design and Validation of a Frugal, Automated, Solid-Phase Peptide Synthesizer

Molecular-Size Fluorescence Emitters

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