Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides

A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies...

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2021-11, Vol.23 (23), p.9549-9553
Main Authors: Xin, Hong, Yuan, Zi-Hang, Yang, Mingyu, Wang, Ming-Hua, Duan, Xin-Hua, Guo, Li-Na
Format: Article
Language:English
Subjects:
Amino acids
Carbonyl compounds
Carbonyl groups
Carbonyls
Glycine
Green chemistry
Peptides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183
cites cdi_FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183
container_end_page 9553
container_issue 23
container_start_page 9549
container_title Green chemistry : an international journal and green chemistry resource : GC
container_volume 23
creator Xin, Hong
Yuan, Zi-Hang
Yang, Mingyu
Wang, Ming-Hua
Duan, Xin-Hua
Guo, Li-Na
description A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies revealed that both a SET event and radical chain propagation were involved in this transformation. A metal free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.
doi_str_mv 10.1039/d1gc03230e
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2604087751</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2604087751</sourcerecordid><originalsourceid>FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183</originalsourceid><addsrcrecordid>eNpF0E1LAzEQBuAgCtbqxbsQ8CZG87XZ7FHWaoWKF8XjkiazNe26uybbQv-90Uo9zTA8zAwvQueM3jAqilvHFpYKLigcoBGTSpCC5_Rw3yt-jE5iXFLKWK7kCL0_w2AaUgeAa7zx0c8bII1ffAzYBb-BFpdkilcwdKZZbRsz-K7FXY0Xzdb6FrCDpNJ0AxGb1uEe-sE7iKfoqDZNhLO_OkZvD5PXckpmL49P5d2MWMH5QJgp5nMHWinK6gw0NVRmuTE249wIZYV26Wmp07-ZtUJKLVyRnKFM5YppMUaXu7196L7WEIdq2a1Dm05WXFFJdZ5nLKmrnbKhizFAXfXBf5qwrRitfoKr7tlj-RvcJOGLHQ7R7t1_sOIbWDxo_g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2604087751</pqid></control><display><type>article</type><title>Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides</title><source>Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)</source><creator>Xin, Hong ; Yuan, Zi-Hang ; Yang, Mingyu ; Wang, Ming-Hua ; Duan, Xin-Hua ; Guo, Li-Na</creator><creatorcontrib>Xin, Hong ; Yuan, Zi-Hang ; Yang, Mingyu ; Wang, Ming-Hua ; Duan, Xin-Hua ; Guo, Li-Na</creatorcontrib><description>A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies revealed that both a SET event and radical chain propagation were involved in this transformation. A metal free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d1gc03230e</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amino acids ; Carbonyl compounds ; Carbonyl groups ; Carbonyls ; Glycine ; Green chemistry ; Peptides</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2021-11, Vol.23 (23), p.9549-9553</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183</citedby><cites>FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183</cites><orcidid>0000-0002-9789-6952 ; 0000-0002-1527-5934</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Xin, Hong</creatorcontrib><creatorcontrib>Yuan, Zi-Hang</creatorcontrib><creatorcontrib>Yang, Mingyu</creatorcontrib><creatorcontrib>Wang, Ming-Hua</creatorcontrib><creatorcontrib>Duan, Xin-Hua</creatorcontrib><creatorcontrib>Guo, Li-Na</creatorcontrib><title>Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies revealed that both a SET event and radical chain propagation were involved in this transformation. A metal free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.</description><subject>Amino acids</subject><subject>Carbonyl compounds</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Glycine</subject><subject>Green chemistry</subject><subject>Peptides</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpF0E1LAzEQBuAgCtbqxbsQ8CZG87XZ7FHWaoWKF8XjkiazNe26uybbQv-90Uo9zTA8zAwvQueM3jAqilvHFpYKLigcoBGTSpCC5_Rw3yt-jE5iXFLKWK7kCL0_w2AaUgeAa7zx0c8bII1ffAzYBb-BFpdkilcwdKZZbRsz-K7FXY0Xzdb6FrCDpNJ0AxGb1uEe-sE7iKfoqDZNhLO_OkZvD5PXckpmL49P5d2MWMH5QJgp5nMHWinK6gw0NVRmuTE249wIZYV26Wmp07-ZtUJKLVyRnKFM5YppMUaXu7196L7WEIdq2a1Dm05WXFFJdZ5nLKmrnbKhizFAXfXBf5qwrRitfoKr7tlj-RvcJOGLHQ7R7t1_sOIbWDxo_g</recordid><startdate>20211129</startdate><enddate>20211129</enddate><creator>Xin, Hong</creator><creator>Yuan, Zi-Hang</creator><creator>Yang, Mingyu</creator><creator>Wang, Ming-Hua</creator><creator>Duan, Xin-Hua</creator><creator>Guo, Li-Na</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-9789-6952</orcidid><orcidid>https://orcid.org/0000-0002-1527-5934</orcidid></search><sort><creationdate>20211129</creationdate><title>Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides</title><author>Xin, Hong ; Yuan, Zi-Hang ; Yang, Mingyu ; Wang, Ming-Hua ; Duan, Xin-Hua ; Guo, Li-Na</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amino acids</topic><topic>Carbonyl compounds</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Glycine</topic><topic>Green chemistry</topic><topic>Peptides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xin, Hong</creatorcontrib><creatorcontrib>Yuan, Zi-Hang</creatorcontrib><creatorcontrib>Yang, Mingyu</creatorcontrib><creatorcontrib>Wang, Ming-Hua</creatorcontrib><creatorcontrib>Duan, Xin-Hua</creatorcontrib><creatorcontrib>Guo, Li-Na</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xin, Hong</au><au>Yuan, Zi-Hang</au><au>Yang, Mingyu</au><au>Wang, Ming-Hua</au><au>Duan, Xin-Hua</au><au>Guo, Li-Na</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2021-11-29</date><risdate>2021</risdate><volume>23</volume><issue>23</issue><spage>9549</spage><epage>9553</epage><pages>9549-9553</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies revealed that both a SET event and radical chain propagation were involved in this transformation. A metal free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1gc03230e</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9789-6952</orcidid><orcidid>https://orcid.org/0000-0002-1527-5934</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1463-9262
ispartof Green chemistry : an international journal and green chemistry resource : GC, 2021-11, Vol.23 (23), p.9549-9553
issn 1463-9262
1463-9270
language eng
recordid cdi_proquest_journals_2604087751
source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Amino acids
Carbonyl compounds
Carbonyl groups
Carbonyls
Glycine
Green chemistry
Peptides
title Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T10%3A53%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Metal-free,%20visible-light%20driven%20C-H%20ketoalkylation%20of%20glycine%20derivatives%20and%20peptides&rft.jtitle=Green%20chemistry%20:%20an%20international%20journal%20and%20green%20chemistry%20resource%20:%20GC&rft.au=Xin,%20Hong&rft.date=2021-11-29&rft.volume=23&rft.issue=23&rft.spage=9549&rft.epage=9553&rft.pages=9549-9553&rft.issn=1463-9262&rft.eissn=1463-9270&rft_id=info:doi/10.1039/d1gc03230e&rft_dat=%3Cproquest_cross%3E2604087751%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c322t-1a9bbde86601f5e80a0457aac522a36c38d926480015cc34483d95e8a01676183%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2604087751&rft_id=info:pmid/&rfr_iscdi=true