Literature DB >> 26712696

Microwave-induced inactivation of DNA-based hybrid catalyst in asymmetric catalysis.

Hua Zhao1, Kai Shen2.   

Abstract

DNA-based hybrid catalysts have gained strong interests in asymmetric reactions. However, to maintain the high enantioselectivity, these reactions are usually conducted at relatively low temperatures (e.g. <5 °C) for 2-3 days. Aiming to improve the reaction's turnover rate, we evaluated microwave irradiation with simultaneous cooling as potential energy source since this method has been widely used to accelerate various chemical and enzymatic reactions. However, our data indicated that microwave irradiation induced an inactivation of DNA-based hybrid catalyst even at low temperatures (such as 5 °C). Circular dichroism (CD) spectra and gel electrophoresis of DNA suggest that microwave exposure degrades DNA molecules and disrupts DNA double-stranded structures, causing changes of DNA-metal ligand binding properties and thus poor DNA catalytic performance.
Copyright © 2015 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  Asymmetric catalysis; DNA-based hybrid catalyst; Michael addition; Microwave irradiation; Simultaneous cooling

Mesh:

Substances:

Year:  2015        PMID: 26712696      PMCID: PMC4724487          DOI: 10.1016/j.ijbiomac.2015.12.048

Source DB:  PubMed          Journal:  Int J Biol Macromol        ISSN: 0141-8130            Impact factor:   6.953


  21 in total

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Authors:  Hua Zhao; Gary A Baker; Shaletha Holmes
Journal:  Org Biomol Chem       Date:  2011-01-31       Impact factor: 3.876

2.  Copper(II)-mediated cross-coupling of arylboronic acids and 2(1H)-pyrazinones facilitated by microwave irradiation with simultaneous cooling.

Authors:  Brajendra Kumar Singh; Prasad Appukkuttan; Stijn Claerhout; Virinder Singh Parmar; Erik Van der Eycken
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

3.  DNA-based catalytic enantioselective michael reactions in water.

Authors:  David Coquière; Ben L Feringa; Gerard Roelfes
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  DNA structural changes caused by microwave radiation.

Authors:  J L Sagripanti; M L Swicord
Journal:  Int J Radiat Biol Relat Stud Phys Chem Med       Date:  1986-07

5.  Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling.

Authors:  Riina K Arvela; Nicholas E Leadbeater
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

6.  DNA-Based Asymmetric Catalysis: Role of Ionic Solvents and Glymes.

Authors:  Hua Zhao; Kai Shen
Journal:  RSC Adv       Date:  2014-01-01       Impact factor: 3.361

7.  Catalytic conjugate additions of carbonyl anions under neutral aqueous conditions.

Authors:  Michael C Myers; Ashwin R Bharadwaj; Benjamin C Milgram; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

8.  Aqueous Ionic Liquids and Deep Eutectic Solvents for Cellulosic Biomass Pretreatment and Saccharification.

Authors:  Shuqian Xia; Gary A Baker; Hao Li; Sudhir Ravula; Hua Zhao
Journal:  RSC Adv       Date:  2014-01-01       Impact factor: 3.361

9.  Enantioselective Friedel-Crafts reactions in water using a DNA-based catalyst.

Authors:  Arnold J Boersma; Ben L Feringa; Gerard Roelfes
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 10.  DNA as a chiral scaffold for asymmetric synthesis.

Authors:  Soyoung Park; Hiroshi Sugiyama
Journal:  Molecules       Date:  2012-10-31       Impact factor: 4.411

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