Fluoroalcohols for chemical modification of biomolecules DOI Creative Commons
Md. Nuruzzaman, Zeinab M. Nizam, Jun Ohata

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100088 - 100088

Published: Aug. 1, 2024

While their broad utility in various chemistry fields were well recognized for decades, fluoroalcohols have recently emerged as a unique solvent system bioconjugation development. This review describes examples and roles of such trifluoroethanol (TFE) hexafluoroisopropanol (HFIP) chemical modification biomolecules polypeptides, nucleic acids, saccharides. Many processes facilitated by notable functions those proton shuttle, reversible adduct formation with reactive species, compatibility electrochemistry/photochemistry. The usefulness the fluoroalcohol solvents can be even promoted its combination different reaction enhancement protein stabilization. collection transformations this is an indication rapid growth solvent-assisted field.

Language: Английский

Metallo-azapeptides: Controlled Metal Chelation to Peptide Backbone Nitrogen DOI
Maxwell O. Bowles, Evan L. Willis,

Meric D. Trombley

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(2), P. 1404 - 1410

Published: Jan. 6, 2025

We present the first approach to controlled metal chelation of peptide backbones, where anchoring site is an aza-amino acid nitrogen and directionality events dictated by acidity neighboring NHs. Selective backbone precludes need for metal-binding side chains and/or free N- or C-termini in peptides. show that presence location impact complex formation report X-ray crystal structures azapeptides bound palladium nickel. Evidence atropisomerism metallo-azapeptides also presented.

Language: Английский

Citations

1
Crafting Unnatural Peptide Macrocycles via Rh(III)-Catalyzed Carboamidation DOI

Christopher W. Lamartina,

Cassandra A. Chartier,

Jillian M. Hirano

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(30), P. 20868 - 20877

Published: July 18, 2024

Contemporary developments in the field of peptide macrocyclization methodology are imperative for enabling advance drug design medicinal chemistry. This report discloses a Rh(III)-catalyzed via carboamidation, reacting acryloyl-peptide-dioxazolone precursors and arylboronic acids to form complex cyclic peptides with concomitant incorporation noncanonical α-amino acids. The diverse modular technology allows expedient access wide variety from 4 15 amino size features simultaneous formation unnatural phenylalanine tyrosine derivatives up >20:1 diastereoselectivity. reaction showcases an expansive substrate scope 45 examples is compatible majority standard protected used Fmoc-solid phase synthesis. applied synthesis multiple peptidomimetic macrocyclic analogs, including cyclosomatostatin gramicidin S.

Language: Английский

Citations

6
Sulfur‐Bridged Pure Organic Ester Clusters Exhibiting Near‐Infrared Fluorescence DOI Open Access
Xiong Liu,

Jiafang Guo,

Zuping Xiong

et al.

Advanced Functional Materials, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

Abstract The development of near‐infrared (NIR) luminophores offers significant potential in the life sciences, yet constructing pure organic clusteroluminescence (CL) from nonconjugated polymers via through‐space interaction (TSI) remains a substantial challenge. Herein, it is revealed that sulfur (S) functions as bridge between isolated ester groups small molecule models, facilitating ( n , π*) transitions. Building on this, RCP1 ‐ RCP5 and P1 P4 are synthesized to produce NIR‐CL luminophores. introduction S enhances chain clustering polyesters modulates inter‐/intra‐chain TSI, while micro‐folding within chains promotes adjacent atoms, resulting marked redshift. Notably, displayed fluorescence peak at 800 nm, extending 883 which sets new record for CL. Additionally, full‐color fluorescent fibers fabricated explored application clusteroluminescent dyes. This work deepens understanding CL mechanisms provides critical insights developing high‐efficiency materials.

Language: Английский

Citations

0
Gold-catalyzed selective modification of peptides: synthesis of cyclic and acyclic peptide derivatives DOI
Guozhi Zhao,

Chengjie Guo,

Dongping Wang

et al.

Gold bulletin, Journal Year: 2025, Volume and Issue: 58(1)

Published: March 20, 2025

Language: Английский

Citations

0
Homogeneous Gold Catalysis: Development and Recent Advances DOI
Tapas Adak

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Abstract Gold catalysis has witnessed remarkable advances over the past decade, with numerous insightful reviews chronicling this progress. However, a comprehensive review addressing developments in field during post‐pandemic COVID era remains notably absent. This aims to bridge that gap by providing an in‐depth analysis of recent studies, shedding light on unique properties gold complexes, particularly intriguing aurophilic interactions distinguish chemistry. The systematically explores latest achievements both mono‐ and dinuclear gold‐catalyzed reactions, focus their applications diverse fields, including redox coupling, asymmetric catalysis, photo‐, electrocatalysis. A special emphasis is placed comparative performance catalysts, latter often exhibiting enhanced catalytic efficiency selectivity certain reactions. By integrating mechanistic insights DFT perspectives representative experimental studies from years, highlights significance synthetic chemistry, identifies emerging trends outlines future directions for field.

Language: Английский

Citations

0
Controlled reversible methionine-selective sulfimidation of peptides DOI

Zeyuan He,

Xiufang Zhao,

Wenyan Gao

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(21)

Published: May 21, 2025

Site-selective chemical peptide manipulation is an effective strategy to understand and regulate structure function. However, methionine-selective modification remains one of the most difficult challenges in chemistry, with notable limited strategies. In this study, we report a general reversible at methionine sites that uses ruthenium-catalyzed sulfimidation peptides. This method provides convenient for late-stage functionalization. The N═S bonds conjugates are reduced presence glutathione, resulting traceless releasing corresponding peptides amides. Practical applications then demonstrated using precise modifications bioactive peptides, stapling linearization peptide-drug conjugates, split-and-pool synthesis. on/off through unique tool chemistry peptide-based drug discovery.

Language: Английский

Citations

0
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization DOI Creative Commons

Xingyu Liu,

О. V. Мykhailenko, Adriana Faraone

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: May 29, 2024

Ethynylbenziodoxol(on)es (EB(X)xs) reagents have emerged as useful for peptide/protein modification due to their versatile reactivity and high selectivity. Herein, we report the successful introduction of ethynylbenziodoxoles (EBxs) on different amino acid building blocks (Lys/Orn/Dap), show compatibility with both solid phase peptide synthesis (SPPS) solution (SPS). The selective incorporation EBx core into sequences enable efficient macrocyclizations under mild conditions topologically unique cyclic bicyclic peptides.

Language: Английский

Citations

1
Chemoselective, Regioselective, and Positionally Selective Fluorogenic Stapling of Unprotected Peptides for Cellular Uptake and Direct Cell Imaging DOI Creative Commons
Naysilla Dayanara, Juliette Froelich,

Pascale Roome

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A mild, rapid, highly selective fluorogenic peptide stapling method is presented resulting in bright green fluorescence. This enables direct assessment of cell uptake via confocal microscopy by virtue the fluorescent staple itself.

Language: Английский

Citations

1
A practical method for the synthesis of small peptides using DCC and HOBt as activators in H2O–THF while avoiding the use of protecting groups DOI Creative Commons

Karina Herrera-Guzmán,

Miguel Ángel Jaime-Vasconcelos,

Eréndira Torales

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(54), P. 39968 - 39976

Published: Jan. 1, 2024

Synthesis of small peptides using DCC and HOBt in H 2 O–THF.

Language: Английский

Citations

1
Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization DOI Creative Commons

Xingyu Liu,

О. V. Мykhailenko, Adriana Faraone

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: May 29, 2024

Abstract Ethynylbenziodoxol(on)es (EB(X)xs) reagents have emerged as useful for peptide/protein modification due to their versatile reactivity and high selectivity. Herein, we report the successful introduction of ethynylbenziodoxoles (EBxs) on different amino acid building blocks (Lys/Orn/Dap), show compatibility with both solid phase peptide synthesis (SPPS) solution (SPS). The selective incorporation EBx core into sequences enable efficient macrocyclizations under mild conditions topologically unique cyclic bicyclic peptides.

Language: Английский

Citations

0