Tag‐Assisted Liquid‐Phase Synthesis of Peptoids

Shin, Dongmin; Seo, Jiwon

doi:10.1002/bkcs.12223

Cited by 4 publications

(5 citation statements)

References 33 publications

(54 reference statements)

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“…If one considers any ring of 2n members containing (n-1) conjugated double bonds then, in principle, irradiation… should furnish an open chain compound containing (n-1 + 1) = n conjugated double bonds. In support of this idea, we have been able to show that irradiation of [10] in ether produces, via [11], the tetraene [12]. Although we have not yet obtained the latter in a state of purity, it shows the correct ultraviolet maxima… Similarly, irradiation of the cyclobutenone [13] gave [14] presumably via 14 a]…" [116] "Quite different considerations apply to rings that contain (2n + 1) members and n conjugated double bonds.…”

Section: Gateway: Pericyclic Reactionsmentioning

confidence: 75%

“…4) But the [4 + 2] cycloaddition will occur thermally (the Diels-Alder reaction) while the photochemical [4 + 2] is rare. [10][11][12][13][14] (eq. 5) Thermal cyclobutene ring openings results in the less stable (E,Z)-1,4-disubstituted-1,3-butadienes.…”

Section: Walter Karl Friedrich Bernhard Hückel (1895-1973)mentioning

confidence: 99%

“…(eq. 4) But the [4+2] cycloaddition will occur thermally (the Diels‐Alder reaction) while the photochemical [4+2] is rare [10–14] . (eq.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Many Chemists Who Could Have Proposed the Woodward‐Hoffmann Rules But Didn't: The Organic Chemists Who Knew of the Smoking Guns**

Seeman

2022

The Chemical Record

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Section: Gateway: Pericyclic Reactionsmentioning

confidence: 75%

Section: Walter Karl Friedrich Bernhard Hückel (1895-1973)mentioning

confidence: 99%

See 1 more Smart Citation

The Many Chemists Who Could Have Proposed the Woodward‐Hoffmann Rules But Didn't: The Organic Chemists Who Knew of the Smoking Guns**

Seeman

2022

The Chemical Record

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“…Lately, as a different strategy, Seo et al applied Tag-assisted liquid phase synthesis to peptoids. [80] Tag-assisted liquid-phase synthesis was developed to expedite the purification process, akin to solid-phase synthesis, while preserving the benefits of the liquid-phase method. In this strategy, a small molecular "Tag" with solubility in a specific solvent is selected.…”

Section: Ring-opening Polymerizationmentioning

confidence: 99%

Well‐Defined Anisotropic Self‐Assembly from Peptoids and Their Biomedical Applications

Okuno

Iwasaki

2023

ChemMedChem

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Peptoids, or poly(N‐substituted glycine)s, hold great promise in biomedical applications because of their biocompatibility, precise synthesis via conventional peptide‐mimicking methods, and readily tunable side chains, which facilitate the control of hydrophobicity and crystallinity. In the past decade, peptoids have been used to create well‐defined self‐assemblies such as vesicles, micelles, sheets, and tubes, which have been scrutinized at the atomic scale using cutting‐edge analytical techniques. This review highlights recent advancements in peptoid synthesis strategies and the development of noteworthy one‐ or two‐dimensional anisotropic self‐assemblies, i. e., nanotubes and nanosheets, exhibiting well‐ordered molecular arrangements. These anisotropic self‐assemblies are formed through the crystallization of peptoid side chains, which can be effortlessly modified via simple synthesis approaches. Moreover, leveraging the protease resistance of peptoids, various biomedical applications are discussed (including phototherapy, enzymatic mimetics, bio‐imaging, and biosensing) that capitalize on the unique properties of anisotropic self‐assembly.

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“…Pyrene-containing Nα chiral submonomers ((S)-1-pyrenylethylamine, s1pye; (R)-1-pyrenylethylamine, r1pye) were synthesized by a previously reported method [34] using Ellman's chiral auxiliaries (tert-butanesulfinamides) (Scheme S1, Supporting Information). Peptoids can be obtained via solid-phase [35] or solution-phase [9,10,36] submonomer synthesis procedures. In the case of the (S)-N-(1-pyrenylethyl)glycine (Ns1pye) homooligomers, a conventional solid-phase peptoid synthesis approach, using bromoacetic acid/DIC coupling, did not allow for bromoacetylation following the second residue, necessitating the use of previously reported solution-phase synthetic methods.…”

Section: Synthesis Of Peptoid Oligomersmentioning

confidence: 99%

Chiral Display of Pyrenes on a Peptoid Backbone: Conformational Homogeneity of Peptoid Controls Excimer Chirality

Oh,

Lee,

Noh

et al. 2023

Small Structures

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Controlling chromophore chirality in three‐dimensional space is crucial for understanding the structure–chiroptical relationship. Such control enables the prediction of ideal materials for use in chiral photonic applications. In this study, optically active multipyrene systems are synthesized on peptoids. Pyrene‐based chiral submonomers, (S)‐ and (R)‐1‐pyrenylethylamine (s1pye and r1pye), are successfully incorporated into peptoids as the respective (S)‐ and (R)‐N‐(1‐pyrenylethyl)glycine (Ns1pye and Nr1pye) units. NMR spectroscopy revealed length‐ and N‐acetylation‐dependent conformational homogeneity enhancement in solution, stabilizing cis‐amides in Ns1pye‐containing peptoids. The X‐ray crystal structure of Ns1pye tetramer displayed a polyproline type‐I (PPI)‐like helix. All of the pyrene‐related absorptions are circular dichroism (CD) active, and the CD signal related to the long‐axis‐polarized transition increased with helical stabilization. Intramolecular excimer generation yielded significant circularly polarized luminescence (CPL) in the excimer emission region. Early‐stage peptoids emitted left‐handed CPL, but upon acquiring a PPI‐like helix character, CPL handedness became inverted. The CPL dissymmetry factor (glum) was comparable or superior (10−2) to that of chiral organic dyes (10−5–10−2). This new class of helical pyrene‐containing peptoids provides a CPL‐active intramolecular excimer, modulating optical activity through peptoid secondary structure homogeneity.

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Tag‐Assisted Liquid‐Phase Synthesis of Peptoids

Cited by 4 publications

References 33 publications

The Many Chemists Who Could Have Proposed the Woodward‐Hoffmann Rules But Didn't: The Organic Chemists Who Knew of the Smoking Guns**

The Many Chemists Who Could Have Proposed the Woodward‐Hoffmann Rules But Didn't: The Organic Chemists Who Knew of the Smoking Guns**

Well‐Defined Anisotropic Self‐Assembly from Peptoids and Their Biomedical Applications

Chiral Display of Pyrenes on a Peptoid Backbone: Conformational Homogeneity of Peptoid Controls Excimer Chirality

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