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Literature DB >> 24059816

A traceless Staudinger reagent to deliver diazirines.

Ali M Ahad¹, Stephanie M Jensen, John C Jewett.

Abstract

A triarylphosphine reagent that reacts with organic azides to install amide-linked diazirines is reported. This traceless Staudinger reagent reacts with complex organic azides to yield amide-linked diazirines, thus expanding the scope of the utility of both azide and diazirine chemistry.

Entities: Chemical Species

Mesh：

Substances：

Year: 2013 PMID： 24059816 PMCID： PMC3857746 DOI： 10.1021/ol402404n

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

22 in total

1. Mechanistic investigation of the staudinger ligation.

Authors: Fiona L Lin; Helen M Hoyt; Herman van Halbeek; Robert G Bergman; Carolyn R Bertozzi
Journal: J Am Chem Soc Date: 2005-03-02 Impact factor: 15.419

2. Mitsunobu and related reactions: advances and applications.

Authors: K C Kumara Swamy; N N Bhuvan Kumar; E Balaraman; K V P Pavan Kumar
Journal: Chem Rev Date: 2009-06 Impact factor: 60.622

3. Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling.

Authors: Zhengqiu Li; Piliang Hao; Lin Li; Chelsea Y J Tan; Xiamin Cheng; Grace Y J Chen; Siu Kwan Sze; Han-Ming Shen; Shao Q Yao
Journal: Angew Chem Int Ed Engl Date: 2013-06-10 Impact factor: 15.336

Review 4. Bioconjugation via azide-Staudinger ligation: an overview.

Authors: Christine I Schilling; Nicole Jung; Moritz Biskup; Ute Schepers; Stefan Bräse
Journal: Chem Soc Rev Date: 2011-06-17 Impact factor: 54.564

5. Photocrosslinking of the signal sequence of nascent preprolactin to the 54-kilodalton polypeptide of the signal recognition particle.

Authors: U C Krieg; P Walter; A E Johnson
Journal: Proc Natl Acad Sci U S A Date: 1986-11 Impact factor: 11.205

3. Enhanced Binding and Reduced Immunogenicity of Glycoconjugates Prepared via Solid-State Photoactivation of Aliphatic Diazirine Carbohydrates.

Authors: Molly D Congdon; Jeffrey C Gildersleeve
Journal: Bioconjug Chem Date: 2020-12-16 Impact factor: 6.069

3 in total

A traceless Staudinger reagent to deliver diazirines.

1. Mechanistic investigation of the staudinger ligation.

2. Mitsunobu and related reactions: advances and applications.

3. Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling.

Review 4. Bioconjugation via azide-Staudinger ligation: an overview.

5. Photocrosslinking of the signal sequence of nascent preprolactin to the 54-kilodalton polypeptide of the signal recognition particle.

Review 6. Photocrosslinking approaches to interactome mapping.

7. Staudinger ligation: a peptide from a thioester and azide.

8. Cell surface engineering by a modified Staudinger reaction.

9. Water-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation.

10. Photocrosslinking of glycoconjugates using metabolically incorporated diazirine-containing sugars.

1. Light-Activated Triazabutadienes for the Modification of a Viral Surface.

2. Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes.

3. Enhanced Binding and Reduced Immunogenicity of Glycoconjugates Prepared via Solid-State Photoactivation of Aliphatic Diazirine Carbohydrates.