Literature DB >> 19585999

Reversible thiazolidine exchange: a new reaction suitable for dynamic combinatorial chemistry.

Cecilia Saiz1, Peter Wipf, Eduardo Manta, Graciela Mahler.   

Abstract

New dynamic combinatorial libraries (DCLs) were generated using the reversible aminothiol exchange reaction of thiazolidines and aromatic aldehydes. The reaction proceeded in aqueous buffered media at pH 4 and room temperature to generate thermodynamically controlled mixtures of heterocycles. The synthesis of an enantiomerically pure thiazolidinyloxazolidine is also reported. The oxazolidine moiety could be exchanged in CH(2)Cl(2) in the presence of catalytic p-TsOH.

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Year:  2009        PMID： 19585999      PMCID： PMC2736333          DOI： 10.1021/ol901104a

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


  12 in total

1.  Dioxadiazadecalin/Salen Tautomeric Macrocycles and Complexes: Prototypal Dynamic Combinatorial Virtual Libraries New Supramolecular Host Systems, Part 12. Part 11: ref. 1. We gratefully acknowledge support by a research grant from the Israel Science Foundation and by an Intel Scholarship (to A.S.), as well as the valuable assistance of Shimon Hauptman with mass spectrometry and Yuri Paskover as an undergraduate research student.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-04       Impact factor: 15.336

2.  Amplification of dynamic chiral crown ether complexes during cyclic acetal formation.

Authors:  Benzion Fuchs; Alshakim Nelson; Alexander Star; J Fraser Stoddart; Sébastien Vidal
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-15       Impact factor: 15.336

3.  From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry.

Authors:  Jean-Marie Lehn
Journal:  Chem Soc Rev       Date:  2006-12-15       Impact factor: 54.564

4.  Systems chemistry.

Authors:  R Frederick Ludlow; Sijbren Otto
Journal:  Chem Soc Rev       Date:  2007-09-03       Impact factor: 54.564

Review 5.  Dynamic combinatorial chemistry: on the road to fulfilling the promise.

Authors:  Sylvain Ladame
Journal:  Org Biomol Chem       Date:  2007-10-29       Impact factor: 3.876

6.  Facile acetal dynamic combinatorial library.

Authors:  Dvora Berkovich-Berger; N Gabriel Lemcoff
Journal:  Chem Commun (Camb)       Date:  2008-02-07       Impact factor: 6.222

7.  Metathesis reaction of formaldehyde acetals: an easy entry into the dynamic covalent chemistry of cyclophane formation.

Authors:  Roberta Cacciapaglia; Stefano Di Stefano; Luigi Mandolini
Journal:  J Am Chem Soc       Date:  2005-10-05       Impact factor: 15.419

8.  Toward novel polyacetals by transacetalation techniques: dendrimeric diacetals.

Authors:  N Gabriel Lemcoff; Benzion Fuchs
Journal:  Org Lett       Date:  2002-03-07       Impact factor: 6.005

9.  Hafnium trifluoromethanesulfonate (hafnium triflate) as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compounds.

Authors:  Yan-Chao Wu; Jieping Zhu
Journal:  J Org Chem       Date:  2008-12-05       Impact factor: 4.354

10.  Tris(thioacetals) from benzene hexathiol: towards covalent self-assembly.

Authors:  Liam R Sutton; Wolfgang A Donaubauer; Frank Hampel; Andreas Hirsch
Journal:  Chem Commun (Camb)       Date:  2004-06-24       Impact factor: 6.222
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  7 in total

1.  Synthesis and ring-chain-ring tautomerism of bisoxazolidines, thiazolidinyloxazolidines, and spirothiazolidines.

Authors:  Cecilia Saiz; Peter Wipf; Graciela Mahler
Journal:  J Org Chem       Date:  2011-06-14       Impact factor: 4.354

2.  Solid-Phase Peptide Capture and Release for Bulk and Single-Molecule Proteomics.

Authors:  Cecil J Howard; Brendan M Floyd; Angela M Bardo; Jagannath Swaminathan; Edward M Marcotte; Eric V Anslyn
Journal:  ACS Chem Biol       Date:  2020-05-14       Impact factor: 5.100

3.  Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors.

Authors:  Cecilia Saiz; Valentina Villamil; Mariano M González; Ma Agustina Rossi; Lorena Martínez; Leopoldo Suescun; Alejandro J Vila; Graciela Mahler
Journal:  Tetrahedron Asymmetry       Date:  2016-11-28

Review 4.  Solid-phase glycan isolation for glycomics analysis.

Authors:  Shuang Yang; Hui Zhang
Journal:  Proteomics Clin Appl       Date:  2012-12       Impact factor: 3.494

5.  Discovering Echinococcus granulosus thioredoxin glutathione reductase inhibitors through site-specific dynamic combinatorial chemistry.

Authors:  Cecilia Saiz; Valerie Castillo; Pablo Fontán; Mariana Bonilla; Gustavo Salinas; Alejandra Rodríguez-Haralambides; S Graciela Mahler
Journal:  Mol Divers       Date:  2013-10-18       Impact factor: 2.943

6.  Antiparallel Dynamic Covalent Chemistries.

Authors:  Bartosz M Matysiak; Piotr Nowak; Ivica Cvrtila; Charalampos G Pappas; Bin Liu; Dávid Komáromy; Sijbren Otto
Journal:  J Am Chem Soc       Date:  2017-05-09       Impact factor: 15.419

7.  Functional Characterization and Structure-Guided Mutational Analysis of the Transsulfuration Enzyme Cystathionine γ-Lyase from Toxoplasma gondii.

Authors:  Elena Maresi; Giacomo Janson; Silvia Fruncillo; Alessandro Paiardini; Rosario Vallone; Paola Dominici; Alessandra Astegno
Journal:  Int J Mol Sci       Date:  2018-07-20       Impact factor: 5.923
  7 in total

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