Literature DB >> 25938936

Optimized diazo scaffold for protein esterification.

Kalie A Mix1, Ronald T Raines1.   

Abstract

The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent.

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Year:  2015        PMID: 25938936      PMCID: PMC4670563          DOI: 10.1021/acs.orglett.5b00840

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


  21 in total

1.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Ribonuclease A.

Authors:  Ronald T. Raines
Journal:  Chem Rev       Date:  1998-05-07       Impact factor: 60.622

Review 3.  Effect of pegylation on pharmaceuticals.

Authors:  J Milton Harris; Robert B Chess
Journal:  Nat Rev Drug Discov       Date:  2003-03       Impact factor: 84.694

4.  STRUCTURAL STUDIES OF RIBONUCLEASE. XVII. A REACTIVE CARBOXYL GROUP IN RIBONUCLEASE.

Authors:  J P RIEHM; H A SCHERAGA
Journal:  Biochemistry       Date:  1965-04       Impact factor: 3.162

5.  Chemical derivatives of alpha-chymotrypsinogen IV. A comparison of the reactions of alpha-chymotrypsinogen and of simple carboxylic acids with diazoacetamide.

Authors:  M S DOSCHER; P E WILCOX
Journal:  J Biol Chem       Date:  1961-05       Impact factor: 5.157

6.  Selective esterase-ester pair for targeting small molecules with cellular specificity.

Authors:  Lin Tian; Yunlei Yang; Laura M Wysocki; Alma C Arnold; Amy Hu; Balaji Ravichandran; Scott M Sternson; Loren L Looger; Luke D Lavis
Journal:  Proc Natl Acad Sci U S A       Date:  2012-03-12       Impact factor: 11.205

7.  Diazo Compounds as Highly Tunable Reactants in 1,3-Dipolar Cycloaddition Reactions with Cycloalkynes().

Authors:  Nicholas A McGrath; Ronald T Raines
Journal:  Chem Sci       Date:  2012-08-02       Impact factor: 9.825

8.  Selective tryptophan modification with rhodium carbenoids in aqueous solution.

Authors:  John M Antos; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

9.  Rhodium-catalyzed cysteine modification with diazo reagents.

Authors:  Rituparna Kundu; Zachary T Ball
Journal:  Chem Commun (Camb)       Date:  2012-11-23       Impact factor: 6.222

10.  Diazo groups endure metabolism and enable chemoselectivity in cellulo.

Authors:  Kristen A Andersen; Matthew R Aronoff; Nicholas A McGrath; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2015-02-16       Impact factor: 15.419

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  16 in total

1.  Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.

Authors:  Eileen G Burke; Brian Gold; Trish T Hoang; Ronald T Raines; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

Review 2.  Diazo Compounds: Versatile Tools for Chemical Biology.

Authors:  Kalie A Mix; Matthew R Aronoff; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2016-10-26       Impact factor: 5.100

3.  Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

Authors:  Nivedita S Mahajani; Rowan I L Meador; Tomas J Smith; Sarah E Canarelli; Arijit A Adhikari; Jigisha P Shah; Christopher M Russo; Daniel R Wallach; Kyle T Howard; Alexandra M Millimaci; John D Chisholm
Journal:  J Org Chem       Date:  2019-05-30       Impact factor: 4.354

4.  Expanding the Scope of Electrophiles Capable of Targeting K-Ras Oncogenes.

Authors:  Lynn M McGregor; Meredith L Jenkins; Caitlin Kerwin; John E Burke; Kevan M Shokat
Journal:  Biochemistry       Date:  2017-06-16       Impact factor: 3.162

5.  1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.

Authors:  Matthew R Aronoff; Brian Gold; Ronald T Raines
Journal:  Org Lett       Date:  2016-03-16       Impact factor: 6.005

6.  Boronic Acid for the Traceless Delivery of Proteins into Cells.

Authors:  Kristen A Andersen; Thomas P Smith; Jo E Lomax; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2015-12-15       Impact factor: 5.100

Review 7.  Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications.

Authors:  Xiaoran Roger Liu; Mengru Mira Zhang; Michael L Gross
Journal:  Chem Rev       Date:  2020-04-22       Impact factor: 60.622

8.  Rapid cycloaddition of a diazo group with an unstrained dipolarophile.

Authors:  Matthew R Aronoff; Brian Gold; Ronald T Raines
Journal:  Tetrahedron Lett       Date:  2016-04-28       Impact factor: 2.415

9.  Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues.

Authors:  Saqib Faisal; Qin Zang; Pradip K Maity; Agnes Brandhofer; Patrick C Kearney; Oliver Reiser; Robert N Grass; Diana Stoianova; Paul R Hanson
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

10.  Cytosolic Delivery of Proteins by Bioreversible Esterification.

Authors:  Kalie A Mix; Jo E Lomax; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2017-10-10       Impact factor: 15.419

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