Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A Cyclopropenethione-Phosphine Ligation for Rapid Biomolecule Labeling.

Literature DB >> 30207474

A Cyclopropenethione-Phosphine Ligation for Rapid Biomolecule Labeling.

Abstract

Cyclopropenethiones are reported as new bioorthogonal reagents. These motifs react readily with substituted phosphines to provide thiocarbonyl adducts. In some cases, the ligations are >300-fold faster than analogous reactions with bioorthogonal cyclopropenones. Dialkyl cyclopropenethiones are also stable in aqueous buffers and can be used for biomolecule labeling in vitro and in cell lysate. The rapid reactivity and biocompatibility of cyclopropenethiones suggest that they will be useful probes for cellular studies.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2018 PMID： 30207474 PMCID： PMC6219755 DOI： 10.1021/acs.orglett.8b02296

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

21 in total

Review 1. Orthogonal bioorthogonal chemistries.

Authors: David M Patterson; Jennifer A Prescher
Journal: Curr Opin Chem Biol Date: 2015-08-10 Impact factor: 8.822

Review 2. An evaluation of peptide-bond isosteres.

Authors: Amit Choudhary; Ronald T Raines
Journal: Chembiochem Date: 2011-07-12 Impact factor: 3.164

3. Thioamide Substitution Selectively Modulates Proteolysis and Receptor Activity of Therapeutic Peptide Hormones.

Authors: Xing Chen; Elizabeth G Mietlicki-Baase; Taylor M Barrett; Lauren E McGrath; Kieran Koch-Laskowski; John J Ferrie; Matthew R Hayes; E James Petersson
Journal: J Am Chem Soc Date: 2017-11-13 Impact factor: 15.419

Review 4. Finding the right (bioorthogonal) chemistry.

Authors: David M Patterson; Lidia A Nazarova; Jennifer A Prescher
Journal: ACS Chem Biol Date: 2014-01-30 Impact factor: 5.100

5. Site-Specific Bioorthogonal Labeling for Fluorescence Imaging of Intracellular Proteins in Living Cells.

Authors: Tao Peng; Howard C Hang
Journal: J Am Chem Soc Date: 2016-10-21 Impact factor: 15.419

6. Native chemical ligation of thioamide-containing peptides: development and application to the synthesis of labeled α-synuclein for misfolding studies.

Authors: Solongo Batjargal; Yanxin J Wang; Jacob M Goldberg; Rebecca F Wissner; E James Petersson
Journal: J Am Chem Soc Date: 2012-04-02 Impact factor: 15.419

7. Constructing New Bioorthogonal Reagents and Reactions.

Authors: R David Row; Jennifer A Prescher
Journal: Acc Chem Res Date: 2018-05-04 Impact factor: 22.384

8. A Bioorthogonal Ligation of Cyclopropenones Mediated by Triarylphosphines.

Authors: Hui-Wen Shih; Jennifer A Prescher
Journal: J Am Chem Soc Date: 2015-08-07 Impact factor: 15.419

9. Cell-type-specific metabolic labeling of nascent proteomes in vivo.

Authors: Beatriz Alvarez-Castelao; Christoph T Schanzenbächer; Cyril Hanus; Caspar Glock; Susanne Tom Dieck; Aline R Dörrbaum; Ina Bartnik; Belquis Nassim-Assir; Elena Ciirdaeva; Anke Mueller; Daniela C Dieterich; David A Tirrell; Julian D Langer; Erin M Schuman
Journal: Nat Biotechnol Date: 2017-11-06 Impact factor: 54.908

10. The effects of thioamide backbone substitution on protein stability: a study in α-helical, β-sheet, and polyproline II helical contexts.

Authors: Christopher R Walters; D Miklos Szantai-Kis; Yitao Zhang; Zachary E Reinert; W Seth Horne; David M Chenoweth; E James Petersson
Journal: Chem Sci Date: 2017-02-08 Impact factor: 9.825

4 in total

1. Developing bioorthogonal probes to span a spectrum of reactivities.

Authors: Sean S Nguyen; Jennifer A Prescher
Journal: Nat Rev Chem Date: 2020-07-21 Impact factor: 34.035

2. Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.

Authors: Tyler K Heiss; Jennifer A Prescher
Journal: J Org Chem Date: 2019-05-28 Impact factor: 4.354

3. Bioorthogonal chemistry.

Authors: Samuel L Scinto; Didier A Bilodeau; Robert Hincapie; Wankyu Lee; Sean S Nguyen; Minghao Xu; Christopher W Am Ende; M G Finn; Kathrin Lang; Qing Lin; John Paul Pezacki; Jennifer A Prescher; Marc S Robillard; Joseph M Fox
Journal: Nat Rev Methods Primers Date: 2021-04-15

4. Phosphine-Catalyzed Dearomative [3 + 2] Cycloaddition of Benzoxazoles with a Cyclopropenone.

Authors: Xingben Wang; Congjun Yu; Iuliana L Atodiresei; Frederic W Patureau
Journal: Org Lett Date: 2022-01-27 Impact factor: 6.005

4 in total