Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids

Dhanya Karipal Padinjare Veedu; Luke A. Connal; Lara R. Malins

doi:10.1021/acs.orglett.3c00988

Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids

Dhanya Karipal Padinjare Veedu, Luke A. Connal, Lara R. Malins^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Arylthioether functional groups serve as effective electroauxiliaries for tunable oxidations. Herein, we disclose the synthesis of second-generation glutamine building blocks bearing 2,4-dimethoxythiophenyl and 2,4-dichlorothiophenyl-derived electroauxiliaries. These building blocks improve SPPS efficiency and enable fine-tuning of the electrochemical window for selective anodic oxidation reactions in comparison to first-generation 4-methoxythiophenyl- and 4-nitrothiophenyl-substituted variants. Installation onto a segment of involucrin, a protein component of human skin, emphasizes the practical application of the new building blocks for iterative functionalizations.

Original language	English
Pages (from-to)	3633-3638
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.3c00988
Publication status	Published - 26 May 2023

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title = "Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids",

abstract = "Arylthioether functional groups serve as effective electroauxiliaries for tunable oxidations. Herein, we disclose the synthesis of second-generation glutamine building blocks bearing 2,4-dimethoxythiophenyl and 2,4-dichlorothiophenyl-derived electroauxiliaries. These building blocks improve SPPS efficiency and enable fine-tuning of the electrochemical window for selective anodic oxidation reactions in comparison to first-generation 4-methoxythiophenyl- and 4-nitrothiophenyl-substituted variants. Installation onto a segment of involucrin, a protein component of human skin, emphasizes the practical application of the new building blocks for iterative functionalizations.",

author = "\{Karipal Padinjare Veedu\}, Dhanya and Connal, \{Luke A.\} and Malins, \{Lara R.\}",

year = "2023",

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doi = "10.1021/acs.orglett.3c00988",

language = "English",

volume = "25",

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journal = "Organic Letters",

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T1 - Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids

AU - Karipal Padinjare Veedu, Dhanya

AU - Connal, Luke A.

AU - Malins, Lara R.

PY - 2023/5/26

Y1 - 2023/5/26

N2 - Arylthioether functional groups serve as effective electroauxiliaries for tunable oxidations. Herein, we disclose the synthesis of second-generation glutamine building blocks bearing 2,4-dimethoxythiophenyl and 2,4-dichlorothiophenyl-derived electroauxiliaries. These building blocks improve SPPS efficiency and enable fine-tuning of the electrochemical window for selective anodic oxidation reactions in comparison to first-generation 4-methoxythiophenyl- and 4-nitrothiophenyl-substituted variants. Installation onto a segment of involucrin, a protein component of human skin, emphasizes the practical application of the new building blocks for iterative functionalizations.

AB - Arylthioether functional groups serve as effective electroauxiliaries for tunable oxidations. Herein, we disclose the synthesis of second-generation glutamine building blocks bearing 2,4-dimethoxythiophenyl and 2,4-dichlorothiophenyl-derived electroauxiliaries. These building blocks improve SPPS efficiency and enable fine-tuning of the electrochemical window for selective anodic oxidation reactions in comparison to first-generation 4-methoxythiophenyl- and 4-nitrothiophenyl-substituted variants. Installation onto a segment of involucrin, a protein component of human skin, emphasizes the practical application of the new building blocks for iterative functionalizations.

UR - https://www.scopus.com/pages/publications/85160457049

U2 - 10.1021/acs.orglett.3c00988

DO - 10.1021/acs.orglett.3c00988

M3 - Article

SN - 1523-7060

VL - 25

SP - 3633

EP - 3638

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Fine-Tuning Electroauxiliary-Mediated Peptide Modifications Using Second-Generation Electroactive Amino Acids

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