Literature DB >> 21486023

Rapid determination of enantiomeric excess of α-chiral cyclohexanones using circular dichroism spectroscopy.

Diana Leung1, Eric V Anslyn.   

Abstract

Ketone handedness was discriminated using circular dichroism (CD) spectroscopy by monitoring the metal-to-ligand charge transfer (MLCT) bands of complexes between [Cu(I)((S)-1)(CH(3)CN)(2)]PF(6) and derivatized α-chiral cyclohexanones (4). This method was able to quantify the enantiomeric excess of unknown samples using a calibration curve, giving an absolute error of ±7%. The analysis was fast, allowing potential application of this assay in high-throughput screening (HTS).

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Year:  2011        PMID： 21486023      PMCID： PMC3097997          DOI： 10.1021/ol2004885

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


  18 in total

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Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-04       Impact factor: 15.336

2.  EMDee: an enzymatic method for determining enantiomeric excess.

Authors:  P Abato; C T Seto
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

Review 3.  Infrared-thermographic screening of the activity and enantioselectivity of enzymes.

Authors:  M T Reetz; M Hermes; M H Becker
Journal:  Appl Microbiol Biotechnol       Date:  2001-05       Impact factor: 4.813

4.  A general method for measurement of enantiomeric excess by using electrooptics in ferroelectric liquid crystals.

Authors:  David M Walba; Lior Eshdat; Eva Korblova; Renfan Shao; Noel A Clark
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  An enantioselective fluorescence sensing assay for quantitative analysis of chiral carboxylic acids and amino acid derivatives.

Authors:  Christian Wolf; Shuanglong Liu; Brian C Reinhardt
Journal:  Chem Commun (Camb)       Date:  2006-09-01       Impact factor: 6.222

6.  Double-cuvette ISES: in situ estimation of enantioselectivity and relative rate for catalyst screening.

Authors:  Sangeeta Dey; Kannan R Karukurichi; Weijun Shen; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

7.  Colour indicator for enantiomeric excess and assignment of the configuration of the major enantiomer of an amino acid ester.

Authors:  Richard A van Delden; Ben L Feringa
Journal:  Chem Commun (Camb)       Date:  2002-01-21       Impact factor: 6.222

8.  A facile circular dichroism protocol for rapid determination of enantiomeric excess and concentration of chiral primary amines.

Authors:  Sonia Nieto; Justin M Dragna; Eric V Anslyn
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

9.  Rapid enantiomeric excess and concentration determination using simple racemic metal complexes.

Authors:  Sonia Nieto; Vincent M Lynch; Eric V Anslyn; Hyunwoo Kim; Jik Chin
Journal:  Org Lett       Date:  2008-10-22       Impact factor: 6.005

10.  Using a lipase as a high-throughput screening method for measuring the enantiomeric excess of allylic acetates.

Authors:  M Burak Onaran; Christopher T Seto
Journal:  J Org Chem       Date:  2003-10-17       Impact factor: 4.354
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  9 in total

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Authors:  Justin M Dragna; Gennaro Pescitelli; Lee Tran; Vincent M Lynch; Eric V Anslyn; Lorenzo Di Bari
Journal:  J Am Chem Soc       Date:  2012-02-22       Impact factor: 15.419

2.  Chiral amine enantiomeric excess determination using self-assembled octahedral Fe(II)-imine complexes.

Authors:  Justin M Dragna; Alexandra M Gade; Lee Tran; Vince M Lynch; Eric V Anslyn
Journal:  Chirality       Date:  2015-02-09       Impact factor: 2.437

3.  The In Situ Enzymatic Screening (ISES) Approach to Reaction Discovery and Catalyst Identification.

Authors:  Robert A Swyka; David B Berkowitz
Journal:  Curr Protoc Chem Biol       Date:  2017-12-14

4.  Hydrazone-based cobalt complexes toward multielectron redox and spin crossover.

Authors:  Wei Huang; Yujie Li; Juan Yong; Yang Liu; Dayu Wu
Journal:  RSC Adv       Date:  2018-05-09       Impact factor: 4.036

5.  Application of a High-Throughput Enantiomeric Excess Optical Assay Involving a Dynamic Covalent Assembly: Parallel Asymmetric Allylation and Ee Sensing of Homoallylic Alcohols.

Authors:  H H Jo; X Gao; L You; E V Anslyn; M J Krische
Journal:  Chem Sci       Date:  2015-07-13       Impact factor: 9.825

6.  Optical Activity and Helicity Enhancement of Highly Sensitive Dinaphthylmethane-Based Stereodynamic Probes for Secondary Alcohols.

Authors:  Tomasz Mądry; Agnieszka Czapik; Marcin Kwit
Journal:  ACS Omega       Date:  2019-02-14

7.  Microscopic origin of the chiroptical response of optical media.

Authors:  Matthew S Davis; Wenqi Zhu; Jay K Lee; Henri J Lezec; Amit Agrawal
Journal:  Sci Adv       Date:  2019-10-11       Impact factor: 14.136

8.  Rapid organocatalytic chirality analysis of amines, amino acids, alcohols, amino alcohols and diols with achiral iso(thio)cyanate probes.

Authors:  Eryn Nelson; Jeffrey S S K Formen; C Wolf
Journal:  Chem Sci       Date:  2021-05-25       Impact factor: 9.825

9.  Discrimination of supramolecular chirality using a protein nanopore.

Authors:  James A Cooper; Stefan Borsley; Paul J Lusby; Scott L Cockroft
Journal:  Chem Sci       Date:  2017-05-11       Impact factor: 9.825
  9 in total

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