Recent developments in the cleavage, functionalization, and conjugation of proteins and peptides at tyrosine residues

Chemical Science, Год журнала: 2023, Номер 14(29), С. 7782 - 7817

Опубликована: Янв. 1, 2023

Peptide and protein selective modification at tyrosine residues has become an exploding field of research as constitutes a robust alternative to lysine cysteine-targeted traditional peptide/protein protocols. This review offers comprehensive summary the latest advances in tyrosine-selective cleavage, functionalization, conjugation peptides proteins from past three years. updated overview complements extensive body work on site-selective proteins, which holds significant relevance across various disciplines, including chemical, biological, medical, material sciences.

Язык: Английский

---

On the Topic of Substrate Scope

Organic Letters, Год журнала: 2022, Номер 24(40), С. 7247 - 7249

Опубликована: Окт. 14, 2022

ADVERTISEMENT RETURN TO ISSUEEditorialNEXTOn the Topic of Substrate ScopeMarisa C. Kozlowski*Marisa KozlowskiDepartment Chemistry, Roy and Diana Vagelos Laboratories, University Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States*Email: [email protected]More by Marisa Kozlowskihttps://orcid.org/0000-0002-4225-7125Cite this: Org. Lett. 2022, 24, 40, 7247–7249Publication Date (Web):October 14, 2022Publication History Received23 September 2022Published online14 October inissue 14 2022https://pubs.acs.org/doi/10.1021/acs.orglett.2c03246https://doi.org/10.1021/acs.orglett.2c03246editorialACS PublicationsCopyright © 2022 American Chemical Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views26432Altmetric-Citations15LEARN ABOUT THESE METRICSArticle Views are COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (1 MB) Get e-AlertscloseSUBJECTS:Addition reactions,Alkyls,Hydrocarbons,Molecules,Organic chemistry e-Alerts

Язык: Английский

---

Pd‐Catalyzed Arylation and Benzylation of Tyrosine at the δ−C(sp²)−H and C(2) Positions: Expanding the Library of Unnatural Tyrosines

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(31)

Опубликована: Июнь 20, 2023

Abstract This paper describes Pd(II)‐catalyzed picolinamide‐directed intermolecular arylation and benzylation of remote δ −C(sp 2 )−H bond (C(2) position) the aryl ring in tyrosine derivatives expansion library unnatural tyrosine. Various racemic enantiopure bis C(2) ( ortho C−H) arylated benzylated were assembled good yields. Removal picolinoyl moiety after C(2)−H assembling tyrosine‐based peptides using tyrosines shown. Tyrosine biaryl amino acids are vital scaffolds medicinal chemistry. Correspondingly, this work is a contribution towards with biaryl‐ or terphenyl diarylmethane‐based scaffolds.

Язык: Английский

---

Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(9), С. 2001 - 2014

Опубликована: Янв. 1, 2023

Excellent diastereoselective access to spirobenzo[ b ]oxepines via a [5 + 2] spirocyclization reaction of ortho -hydroxyacetophenones and 2-aroyl-1-chlorocyclopropanecarboxylates triggered by Cs 2 CO 3 was developed.

Язык: Английский

---

Indole-Fused Benzoxepine Synthesis via Visible-Light-Driven Aerobic Dehydrogenative [5 + 2] Annulation

Organic Letters, Год журнала: 2023, Номер 25(46), С. 8258 - 8262

Опубликована: Ноя. 13, 2023

A photocatalyzed oxidative dehydrogenative annulation between 2-(1H-indol-2-yl)phenols and alkenylphenols is presented. Various indole-fused benzoxepines can be obtained at room temperature using atom-efficient strategies. This method not only avoids the use of stoichiometric amounts oxidants but also exhibits excellent atom economy by generating H2O as theoretical byproduct.

Язык: Английский

---

Conjugated Olefin Enabled Rollover Cyclometallation of Distant C‐H Bonds: Regioselective Annulation of o‐Alkenyl Phenols with Alkynes

Chemistry - A European Journal, Год журнала: 2023, Номер 29(70)

Опубликована: Окт. 11, 2023

Although challenging, the distant C-H functionalization with precision is quite rewarding and has long been intriguing. Tailoring an appropriate template accomplishes job but prerequisite sets limitation. We herein unveil our discovery of annulation alkynes on to two (from directing group) bonds through rollover cyclometallation assisted by conjugated C=C bond. The follows a concomitant cyclization rare triple functionalization. totally regioselective array unsymmetrical alkynes, taking leverage extended conjugation or tertiary hydroxyl co-ordination. mechanism supported control experiments, KIE & labelling studies Mass spectrometry.

Язык: Английский

---

Iridium-catalyzed diacylmethylation of tyrosines and its peptides with sulfoxonium ylides

Chemical Communications, Год журнала: 2024, Номер 60(59), С. 7622 - 7625

Опубликована: Янв. 1, 2024

Pyridyloxy-directed Ir( iii )-catalyzed diacylmethylation of protected tyrosines was achieved with alkyl and (hetero)aryl sulfoxonium ylides, furnishing tyrosine-based unnatural amino acids in good yields.

Язык: Английский

---