Total Synthesis and Structural Characterization of Caveolin‐1

Hojo, Hironobu; Takei, Toshiki; Asahina, Yuya; Okumura, Nobuaki; Takao, Toshifumi; So, Masatomo; Suetake, Isao; Sato, Takeshi; Kawamoto, Akihiro; Hirabayashi, Yoshio

doi:10.1002/ange.202100826

Cited by 4 publications

(2 citation statements)

References 49 publications

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“…The lability of S ‐palmitoyl thioester renders its synthesis rather difficult and challenging. Access to the S ‐palmitoylated peptide has been achieved by direct Fmoc‐SPPS [32a] or post‐Fmoc‐SPPS‐modification; [10a, 32b,c] however, the length of the peptide was limited, or a complicated protocol was required. Additionally, the use of NCL for peptides containing S ‐palmitoylation modification was precluded, due to the reactivity of the S ‐palmitoyl thioester towards the thiol species in the NCL system.…”

Section: Resultsmentioning

confidence: 99%

Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters

et al. 2022

Angew Chem Int Ed

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Chemical synthesis of proteins bearing base‐labile post‐translational modifications (PTMs) is a challenging task. For instance, O‐acetylation and S‐palmitoylation PTMs cannot survive Fmoc removal conditions during Fmoc‐solid phase peptide synthesis (SPPS). In this work, we developed a new Boc‐SPPS‐based strategy for the synthesis of peptide C‐terminal salicylaldehyde (SAL) esters, which are the key reaction partner in Ser/Thr ligation and Cys/Pen ligation. The strategy utilized the semicarbazone‐modified aminomethyl (AM) resin, which could support the Boc‐SPPS and release the peptide SAL ester upon treatment with TFA/H2O and pyruvic acid. The non‐oxidative aldehyde regeneration was fully compatible with all the canonical amino acids. Armed with this strategy, we finished the syntheses of the O‐acetylated protein histone H3(S10ac, T22ac) and the hydrophobic S‐palmitoylated peptide derived from caveolin‐1.

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Section: Resultsmentioning

confidence: 99%

Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters

et al. 2022

Angew Chem Int Ed

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show abstract

Section: Resultsmentioning

confidence: 99%

Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters

et al. 2022

Angewandte Chemie

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Chemical synthesis of proteins bearing baselabile post-translational modifications (PTMs) is a challenging task. For instance, O-acetylation and Spalmitoylation PTMs cannot survive Fmoc removal conditions during Fmoc-solid phase peptide synthesis (SPPS). In this work, we developed a new Boc-SPPSbased strategy for the synthesis of peptide C-terminal salicylaldehyde (SAL) esters, which are the key reaction partner in Ser/Thr ligation and Cys/Pen ligation. The strategy utilized the semicarbazone-modified aminomethyl (AM) resin, which could support the Boc-SPPS and release the peptide SAL ester upon treatment with TFA/H 2 O and pyruvic acid. The non-oxidative aldehyde regeneration was fully compatible with all the canonical amino acids. Armed with this strategy, we finished the syntheses of the O-acetylated protein histone H3(S10ac, T22ac) and the hydrophobic Spalmitoylated peptide derived from caveolin-1.

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Chemische Synthese und Semisynthese von lipidierten Proteinen

Hanna¹,

Kriegesmann

Dowman

et al. 2022

Angewandte Chemie

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Lipidierung ist eine ubiquitäre Modifikation von Peptiden und Proteinen, die entweder co‐ oder posttranslational auftreten kann. Für die Vielzahl von Lipidklassen wurde gezeigt, dass diese viele entscheidende biologische Aktivitäten, z. B. die Regulierung der Signalweiterleitung, Zell‐Zell‐Adhäsion sowie die Anlagerung von Proteinen an Lipid‐Rafts und Phospholipidmembranen, beeinflussen. Während die Natur Enzyme nutzt, um Lipidmodifikationen in Proteine einzubringen, ist ihre Nutzung für die chemoenzymatische Herstellung von lipidierten Proteinen häufig ineffizient. Eine Alternative ist die Kombination moderner synthetischer und semisynthetischer Techniken, um lipidierte Proteine in reiner und homogen modifizierter Form zu erhalten. Dieser Aufsatz erörtert Fortschritte in der Entwicklung der Lipidierungs‐ und Ligationschemie und deren Anwendung in der Synthese und Semisynthese homogen lipidierter Proteine, die es ermöglichen, den Einfluss dieser Modifikationen auf die Proteinstruktur und ‐funktion zu untersuchen.

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Total Synthesis and Structural Characterization of Caveolin‐1

Cited by 4 publications

References 49 publications

Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters

Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters

Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters

Chemische Synthese und Semisynthese von lipidierten Proteinen

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