Late‐Stage, Stereoretentive, and Site‐Selective Modification of Synthetic Peptides by Using Photoredox Catalysis

to related objects

Abstract: Late‐stage functionalisation is an attractive method to generate peptide analogues containing non‐natural residues. It is shown that cysteine residues can be activated as Crich‐type thioethers, either by alkylation of a synthetic cysteine‐continuing peptide or by incorporation of a modified cysteine unit into solid phase or solution phase peptide synthesis. Photoredox catalysed reaction of the thioether generates an alanyl radical intermediate in a stereoretentive and site‐selective manner, even in the presence of free cysteine residues. The radical can react with non‐activated alkenes to form non‐natural residues bearing aliphatic, hydrophobic units. A method to avoid unwanted alkylation of amine residues was identified and the process was applied to the functionalization of both linear and cyclic synthetic peptides.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Late‐Stage, Stereoretentive, and Site‐Selective Modification of Synthetic Peptides by Using Photoredox Catalysis ; day:31 ; month:05 ; year:2023 ; extent:12
Chemistry - a European journal ; (31.05.2023) (gesamt 12)

Creator: Flitcroft, Claire E.
Jolliffe, Katrina A.
McErlean, Christopher S. P.

DOI: 10.1002/chem.202301083

URN: urn:nbn:de:101:1-2023060115281028577917

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:51 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Flitcroft, Claire E.
Jolliffe, Katrina A.
McErlean, Christopher S. P.

Other Objects (12)

Site‐selective Photoredox‐Catalyzed Late‐stage Benzylic Hydrogen Isotope Exchange

Copper-Mediated Late-Stage Fluorination of Arenes Using Photoredox Catalysis

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Site‐Selective, Remote sp 3 C−H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis

Organic synthesis using photoredox catalysis

Photoredox Catalysis Using Copper Complexes

Cooperative Photoredox Catalysis Under Confinement

Organic synthesis using photoredox catalysis

Enzymatic Late‐Stage Halogenation of Peptides

Photoredox C–H functionalization leads the site-selective phenylalanine bioconjugation

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Site‐selective Photoredox‐Catalyzed Late‐stage Benzylic Hydrogen Isotope Exchange

Copper-Mediated Late-Stage Fluorination of Arenes Using Photoredox Catalysis

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Site‐Selective, Remote sp 3 C−H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis

Organic synthesis using photoredox catalysis

Photoredox Catalysis Using Copper Complexes

Cooperative Photoredox Catalysis Under Confinement

Organic synthesis using photoredox catalysis

Enzymatic Late‐Stage Halogenation of Peptides

Photoredox C–H functionalization leads the site-selective phenylalanine bioconjugation

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Site‐selective Photoredox‐Catalyzed Late‐stage Benzylic Hydrogen Isotope Exchange

Copper-Mediated Late-Stage Fluorination of Arenes Using Photoredox Catalysis

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Site‐Selective, Remote sp 3 C−H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis

Organic synthesis using photoredox catalysis

Photoredox Catalysis Using Copper Complexes

Cooperative Photoredox Catalysis Under Confinement

Organic synthesis using photoredox catalysis

Enzymatic Late‐Stage Halogenation of Peptides

Photoredox C–H functionalization leads the site-selective phenylalanine bioconjugation

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.

Late‐Stage, Stereoretentive, and Site‐Selective Modification of Synthetic Peptides by Using Photoredox Catalysis

Object Details

References and Relationships

Contributors, Places and Time

Further information

Data provider

Associated

Other Objects (12)

Site‐selective Photoredox‐Catalyzed Late‐stage Benzylic Hydrogen Isotope Exchange

Copper-Mediated Late-Stage Fluorination of Arenes Using Photoredox Catalysis

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Site‐Selective, Remote sp 3 C−H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis

Organic synthesis using photoredox catalysis

Photoredox Catalysis Using Copper Complexes

Cooperative Photoredox Catalysis Under Confinement

Organic synthesis using photoredox catalysis

Enzymatic Late‐Stage Halogenation of Peptides

Photoredox C–H functionalization leads the site-selective phenylalanine bioconjugation

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Site‐selective Photoredox‐Catalyzed Late‐stage Benzylic Hydrogen Isotope Exchange

Copper-Mediated Late-Stage Fluorination of Arenes Using Photoredox Catalysis

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Site‐Selective, Remote sp 3 C−H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis

Organic synthesis using photoredox catalysis

Photoredox Catalysis Using Copper Complexes

Cooperative Photoredox Catalysis Under Confinement

Organic synthesis using photoredox catalysis

Enzymatic Late‐Stage Halogenation of Peptides

Photoredox C–H functionalization leads the site-selective phenylalanine bioconjugation

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Site‐selective Photoredox‐Catalyzed Late‐stage Benzylic Hydrogen Isotope Exchange

Copper-Mediated Late-Stage Fluorination of Arenes Using Photoredox Catalysis

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation

Site‐Selective, Remote sp 3 C−H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis

Organic synthesis using photoredox catalysis

Photoredox Catalysis Using Copper Complexes

Cooperative Photoredox Catalysis Under Confinement

Organic synthesis using photoredox catalysis

Enzymatic Late‐Stage Halogenation of Peptides

Photoredox C–H functionalization leads the site-selective phenylalanine bioconjugation

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Related objects

Reset password