Literature DB >> 28005341

Sensitive and Accurate 13C Kinetic Isotope Effect Measurements Enabled by Polarization Transfer.

Eugene E Kwan1, Yongho Park1, Harrison A Besser1, Thayer L Anderson1, Eric N Jacobsen1.   

Abstract

Polarization transfer is demonstrated as a sensitive technique for the measurement of isotopic fractionation of protonated carbons at natural abundance. This method allows kinetic isotope effects (KIEs) to be determined with substantially less material or shorter acquisition time compared with traditional experiments. Computations quantitatively reproduce the KIEs in a Diels-Alder reaction and a catalytic glycosylation. The glycosylation is shown to occur by an effectively concerted mechanism.

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Year:  2016        PMID： 28005341      PMCID： PMC5674980          DOI： 10.1021/jacs.6b10621

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

1.  Mechanism of ene reactions of singlet oxygen. A two-step no-intermediate mechanism.

Authors:  Daniel A Singleton; Chao Hang; Michael J Szymanski; Matthew P Meyer; Andrew G Leach; Keith T Kuwata; Jenny S Chen; Alexander Greer; Christopher S Foote; K N Houk
Journal:  J Am Chem Soc       Date:  2003-02-05       Impact factor: 15.419

2.  Quantitative (13)C NMR spectroscopy using refocused constant-time INEPT, Q-INEPT-CT.

Authors:  A V Mäkelä; I Kilpeläinen; S Heikkinen
Journal:  J Magn Reson       Date:  2010-02-23       Impact factor: 2.229

3.  A theoretical investigation of alpha-carbon kinetic isotope effects and their relationship to the transition-state structure of S(N)2 reactions.

Authors:  O Matsson; A Dybala-Defratyka; M Rostkowski; P Paneth; K C Westaway
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

4.  Isotope effects and heavy-atom tunneling in the Roush allylboration of aldehydes.

Authors:  Mathew J Vetticatt; Daniel A Singleton
Journal:  Org Lett       Date:  2012-04-16       Impact factor: 6.005

5.  Measurements of heavy-atom isotope effects using 1H NMR spectroscopy.

Authors:  Anna Pabis; Rafał Kamiński; Grzegorz Ciepielowski; Stefan Jankowski; Piotr Paneth
Journal:  J Org Chem       Date:  2011-08-31       Impact factor: 4.354

6.  Mechanistic study of the SmI2/H2O/amine-mediated reduction of alkyl halides: amine base strength (pKBH+) dependent rate.

Authors:  Anders Dahlén; Göran Hilmersson
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

7.  N-Heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with α,β-unsaturated acid fluorides.

Authors:  Sarah J Ryan; Lisa Candish; David W Lupton
Journal:  J Am Chem Soc       Date:  2011-03-10       Impact factor: 15.419

8.  Transition-state geometry measurements from (13)c isotope effects. The experimental transition state for the epoxidation of alkenes with oxaziridines.

Authors:  Jennifer S Hirschi; Tetsuya Takeya; Chao Hang; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

9.  Highly precise measurement of kinetic isotope effects using 1H-detected 2D [13C,1H]-HSQC NMR spectroscopy.

Authors:  Kathryn A Manning; Bharathwaj Sathyamoorthy; Alexander Eletsky; Thomas Szyperski; Andrew S Murkin
Journal:  J Am Chem Soc       Date:  2012-12-11       Impact factor: 15.419

10.  Sensitivity-enhanced quantitative 13C NMR spectroscopy via cancellation of 1J(CH) dependence in DEPT polarization transfers.

Authors:  Terry J Henderson
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419
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  11 in total

Review 1.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

2.  Keeping Track of the Electrons.

Authors:  Erika L Lucas; Elizabeth R Jarvo
Journal:  Acc Chem Res       Date:  2018-01-24       Impact factor: 22.384

3.  Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Authors:  Samuel M Levi; Qiuhan Li; Andreas R Rötheli; Eric N Jacobsen
Journal:  Proc Natl Acad Sci U S A       Date:  2018-12-17       Impact factor: 11.205

4.  Mimicry of the proton wire mechanism of enzymes inside a supramolecular capsule enables β-selective O-glycosylations.

Authors:  Tian-Ren Li; Fabian Huck; GiovanniMaria Piccini; Konrad Tiefenbacher
Journal:  Nat Chem       Date:  2022-07-07       Impact factor: 24.274

5.  Blue Light Photocatalytic Glycosylation without Electrophilic Additives.

Authors:  Peng Wen; David Crich
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

6.  Synthesis of Conformationally-Locked cis- and trans-Bicyclo[4.4.0] Mono-, Di-, and Trioxadecane Modifications of Galacto- and Glucopyranose; Experimental Limiting 3JH,H Coupling Constants for the Estimation of Carbohydrate Side Chain Populations and Beyond.

Authors:  Harsha Amarasekara; Suresh Dharuman; Takayuki Kato; David Crich
Journal:  J Org Chem       Date:  2018-01-03       Impact factor: 4.354

7.  Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation.

Authors:  Jesse Ling; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336

8.  Enantioselective Aryl-Iodide-Catalyzed Wagner-Meerwein Rearrangements.

Authors:  Hayden A Sharma; Katrina M Mennie; Eugene E Kwan; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-09-03       Impact factor: 15.419

9.  En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.

Authors:  David Crich
Journal:  J Am Chem Soc       Date:  2020-12-22       Impact factor: 15.419

10.  Concerted nucleophilic aromatic substitutions.

Authors:  Eugene E Kwan; Yuwen Zeng; Harrison A Besser; Eric N Jacobsen
Journal:  Nat Chem       Date:  2018-07-16       Impact factor: 24.427
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