Literature DB >> 22936329

Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release.

R Adam Mosey1, Paul E Floreancig.   

Abstract

A series of α-alkoxy carbamates that cleave under mild conditions to release alcohols has been synthesized through a multicomponent process. The relationship between structural features in these compounds and the rate of alcohol release in the presence of basic hydrogen peroxide has been studied. The preparation of carbamates that cleave under other conditions has been demonstrated.

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Year:  2012        PMID： 22936329      PMCID： PMC3532511          DOI： 10.1039/c2ob26571k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  34 in total

Review 1.  Targeting large molecules to mitochondria.

Authors:  A Muratovska; R N Lightowlers; R W Taylor; J A Wilce; M P Murphy
Journal:  Adv Drug Deliv Rev       Date:  2001-07-02       Impact factor: 15.470

2.  A unique paradigm for a Turn-ON near-infrared cyanine-based probe: noninvasive intravital optical imaging of hydrogen peroxide.

Authors:  Naama Karton-Lifshin; Ehud Segal; Liora Omer; Moshe Portnoy; Ronit Satchi-Fainaro; Doron Shabat
Journal:  J Am Chem Soc       Date:  2011-06-22       Impact factor: 15.419

3.  Boronate oxidation as a bioorthogonal reaction approach for studying the chemistry of hydrogen peroxide in living systems.

Authors:  Alexander R Lippert; Genevieve C Van de Bittner; Christopher J Chang
Journal:  Acc Chem Res       Date:  2011-08-11       Impact factor: 22.384

4.  Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogs.

Authors:  Shuangyi Wan; Fanghui Wu; Jason C Rech; Michael E Green; Raghavan Balachandran; W Seth Horne; Billy W Day; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

5.  Distribution of electrical potential, pH, free Ca2+, and volume inside cultured adult rabbit cardiac myocytes during chemical hypoxia: a multiparameter digitized confocal microscopic study.

Authors:  E Chacon; J M Reece; A L Nieminen; G Zahrebelski; B Herman; J J Lemasters
Journal:  Biophys J       Date:  1994-04       Impact factor: 4.033

6.  Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.

Authors:  Chunliang Lu; Qing Xiao; Paul E Floreancig
Journal:  Org Lett       Date:  2010-10-20       Impact factor: 6.005

7.  Selective targeting of an antioxidant to mitochondria.

Authors:  R A Smith; C M Porteous; C V Coulter; M P Murphy
Journal:  Eur J Biochem       Date:  1999-08

8.  Lipid antioxidants: free radical scavenging versus regulation of enzymatic lipid peroxidation.

Authors:  Alejandro K Samhan-Arias; Yulia Y Tyurina; Valerian E Kagan
Journal:  J Clin Biochem Nutr       Date:  2010-12-28       Impact factor: 3.114

9.  An ICT-based approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells.

Authors:  Duangkhae Srikun; Evan W Miller; Dylan W Domaille; Christopher J Chang
Journal:  J Am Chem Soc       Date:  2008-03-13       Impact factor: 15.419

Review 10.  Targeting mitochondria.

Authors:  Adam T Hoye; Jennifer E Davoren; Peter Wipf; Mitchell P Fink; Valerian E Kagan
Journal:  Acc Chem Res       Date:  2008-01       Impact factor: 22.384
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  9 in total

1.  Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation.

Authors:  Ramsey D Hanna; Yuta Naro; Alexander Deiters; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2016-09-30       Impact factor: 15.419

2.  Small Molecule Control of Morpholino Antisense Oligonucleotide Function through Staudinger Reduction.

Authors:  Kristie Darrah; Joshua Wesalo; Bradley Lukasak; Michael Tsang; James K Chen; Alexander Deiters
Journal:  J Am Chem Soc       Date:  2021-10-27       Impact factor: 16.383

3.  Stereocontrolled cyanohydrin ether synthesis through chiral Brønsted acid-mediated vinyl ether hydrocyanation.

Authors:  Chunliang Lu; Xiaoge Su; Paul E Floreancig
Journal:  J Org Chem       Date:  2013-09-04       Impact factor: 4.354

4.  A Strategy for Minimizing Background Signal in Autoinductive Signal Amplification Reactions for Point-of-Need Assays.

Authors:  Adam D Brooks; Kimy Yeung; Gregory G Lewis; Scott T Phillips
Journal:  Anal Methods       Date:  2015-03-06       Impact factor: 2.896

5.  Design, Synthesis, and Characterization of Small-Molecule Reagents That Cooperatively Provide Dual Readouts for Triaging and, When Necessary, Quantifying Point-of-Need Enzyme Assays.

Authors:  Adam D Brooks; Hemakesh Mohapatra; Scott T Phillips
Journal:  J Org Chem       Date:  2015-10-16       Impact factor: 4.354

6.  Phosphine-Activated Lysine Analogues for Fast Chemical Control of Protein Subcellular Localization and Protein SUMOylation.

Authors:  Joshua S Wesalo; Ji Luo; Kunihiko Morihiro; Jihe Liu; Alexander Deiters
Journal:  Chembiochem       Date:  2019-10-30       Impact factor: 3.164

7.  Zinc Chloride-Catalyzed Synthesis of Carbamates: An Application for the Synthesis of the Anti-Alzheimer's Drug Rivastigmine.

Authors:  Manoj Gayke; Nirbhay Hirapara; Hanuman Narode; Siddhanath D Bhosle; Rajesh S Bhosale; Jhillu Singh Yadav
Journal:  ACS Omega       Date:  2022-09-26

8.  Mechanically Triggered Release of Functionally Diverse Molecular Payloads from Masked 2-Furylcarbinol Derivatives.

Authors:  Xiaoran Hu; Tian Zeng; Corey C Husic; Maxwell J Robb
Journal:  ACS Cent Sci       Date:  2021-07-14       Impact factor: 14.553

9.  Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation.

Authors:  Xhenti Ferhati; Marina Salas-Cubero; Pablo Garrido; Josune García-Sanmartín; Ana Guerreiro; Alberto Avenoza; Jesús H Busto; Jesús M Peregrina; Alfredo Martínez; Ester Jiménez-Moreno; Gonçalo J L Bernardes; Francisco Corzana
Journal:  Org Lett       Date:  2021-10-25       Impact factor: 6.005
  9 in total

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