Literature DB >> 29115835

CITU: A Peptide and Decarboxylative Coupling Reagent.

Justine N deGruyter1, Lara R Malins1, Laurin Wimmer1, Khalyd J Clay1, Javier Lopez-Ogalla1, Tian Qin1, Josep Cornella1, Zhiqing Liu2, Guanda Che2, Denghui Bao2, Jason M Stevens3, Jennifer X Qiao4, Martin P Allen4, Michael A Poss4, Phil S Baran1.   

Abstract

Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is disclosed as a convenient and economical reagent for both acylation and decarboxylative cross-coupling chemistries. Within the former set of reactions, CITU displays reactivity similar to that of common coupling reagents, but with increased safety and reduced cost. Within the latter, increased yields, more rapid conversion, and a simplified procedure are possible across a range of reported decarboxylative transformations.

Entities:  

Mesh：

Substances：

Year:  2017        PMID： 29115835      PMCID： PMC5792187          DOI： 10.1021/acs.orglett.7b03121

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


  14 in total

1.  Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?

Authors:  Dean G Brown; Jonas Boström
Journal:  J Med Chem       Date:  2015-12-01       Impact factor: 7.446

2.  Benzotriazole-assisted solid-phase assembly of Leu-enkephalin, amyloid beta segment 34-42, and other "difficult" peptide sequences.

Authors:  Alan R Katritzky; Danniebelle N Haase; Jodie V Johnson; Alfred Chung
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

3.  Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

Authors:  Ramon Subirós-Funosas; Rafel Prohens; Rafael Barbas; Ayman El-Faham; Fernando Albericio
Journal:  Chemistry       Date:  2009-09-21       Impact factor: 5.236

Review 4.  Peptide coupling reagents, more than a letter soup.

Authors:  Ayman El-Faham; Fernando Albericio
Journal:  Chem Rev       Date:  2011-08-26       Impact factor: 60.622

5.  A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

Authors:  Tian Qin; Josep Cornella; Chao Li; Lara R Malins; Jacob T Edwards; Shuhei Kawamura; Brad D Maxwell; Martin D Eastgate; Phil S Baran
Journal:  Science       Date:  2016-04-21       Impact factor: 47.728

6.  Alkyl-(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis.

Authors:  Frederik Sandfort; Matthew J O'Neill; Josep Cornella; Laurin Wimmer; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-10       Impact factor: 15.336

7.  S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium Hexafluorophosphate. A New Reagent for Preparing Hindered Barton Esters.

Authors:  Philip Garner; James T. Anderson; Subhakar Dey; Wiley J. Youngs; Kevin Galat
Journal:  J Org Chem       Date:  1998-08-21       Impact factor: 4.354

8.  Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.

Authors:  Jie Wang; Tian Qin; Tie-Gen Chen; Laurin Wimmer; Jacob T Edwards; Josep Cornella; Benjamin Vokits; Scott A Shaw; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-06       Impact factor: 15.336

9.  Decarboxylative alkenylation.

Authors:  Jacob T Edwards; Rohan R Merchant; Kyle S McClymont; Kyle W Knouse; Tian Qin; Lara R Malins; Benjamin Vokits; Scott A Shaw; Deng-Hui Bao; Fu-Liang Wei; Ting Zhou; Martin D Eastgate; Phil S Baran
Journal:  Nature       Date:  2017-04-19       Impact factor: 49.962

10.  Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

Authors:  Ellen M Sletten; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
View more
  9 in total

1.  Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.

Authors:  Amira H Dardir; Nilay Hazari; Scott J Miller; Christopher R Shugrue
Journal:  Org Lett       Date:  2019-07-10       Impact factor: 6.005

2.  Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters.

Authors:  Jiang Wang; Brian P Cary; Peyton D Beyer; Samuel H Gellman; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-30       Impact factor: 15.336

3.  Radical Retrosynthesis.

Authors:  Joel M Smith; Stephen J Harwood; Phil S Baran
Journal:  Acc Chem Res       Date:  2018-08-02       Impact factor: 22.384

4.  From d- to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation.

Authors:  I C Steven Wan; Martin D Witte; Adriaan J Minnaard
Journal:  Org Lett       Date:  2019-09-12       Impact factor: 6.005

5.  Polymer End Group Control through a Decarboxylative Cobalt-Mediated Radical Polymerization: New Avenues for Synthesizing Peptide, Protein, and Nanomaterial Conjugates.

Authors:  Meri Ayurini; Peter G Chandler; Paul D O'Leary; Ruoxin Wang; David Rudd; Karen D Milewska; Lara R Malins; Ashley M Buckle; Joel F Hooper
Journal:  JACS Au       Date:  2021-11-30

6.  A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C.

Authors:  Luka Raguž; Chia-Chi Peng; Marcel Kaiser; Helmar Görls; Christine Beemelmanns
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-07       Impact factor: 16.823

7.  Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis.

Authors:  Daniel Leichnitz; Chia-Chi Peng; Luka Raguž; Florentine U N Rutaganira; Theresa Jautzus; Lars Regestein; Nicole King; Christine Beemelmanns
Journal:  Chemistry       Date:  2021-12-28       Impact factor: 5.020

8.  Total synthesis of biseokeaniamides A-C and late-stage electrochemically-enabled peptide analogue synthesis.

Authors:  Yutong Lin; Lara R Malins
Journal:  Chem Sci       Date:  2020-07-30       Impact factor: 9.825

Review 9.  Radical-Based Synthesis and Modification of Amino Acids.

Authors:  Francisco José Aguilar Troyano; Kay Merkens; Khadijah Anwar; Adrián Gómez-Suárez
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-04       Impact factor: 15.336
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.