Literature DB >> 18612332

Reaction of an Introverted Carboxylic Acid with Carbodiimide.

Tetsuo Iwasawa1, Paul Wash, Christoph Gibson, Julius Rebek.   

Abstract

The reaction of carboxylic acids with carbodiimides is reviewed, and an "introverted" carboxylic acid is proposed as a means of trapping reactive intermediates along the reaction pathway. The introverted acid is a cavitand with the carboxylic function directed toward the floor of the cavity. Its reaction with diisopropyl carboodiimide gives a covalent adduct that is either the elusive O-acylisourea or the commonly encountered N-acylurea.

Entities:  

Year:  2007        PMID： 18612332      PMCID： PMC2031843          DOI： 10.1016/j.tet.2007.03.075

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  17 in total

1.  Molecular Recognition with Introverted Functionality We are grateful for financial support from the Skaggs Research Foundation and the National Institutes of Health. We thank Prof. Dmitry Rudkevich and Dr. Paul Wash and Dr. Laura Pasternack for helpful advice and instrumental support.

Authors:  A R Renslo; J Rebek
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-15       Impact factor: 15.336

2.  Amplification by compartmentalization.

Authors:  Jian Chen; Steffi Körner; Stephen L Craig; Dmitry M Rudkevich; Julius Rebek
Journal:  Nature       Date:  2002-01-24       Impact factor: 49.962

3.  Chemical amplification with encapsulated reagents.

Authors:  Jian Chen; Steffi Körner; Stephen L Craig; Shirley Lin; Dmitry M Rudkevich; Julius Rebek
Journal:  Proc Natl Acad Sci U S A       Date:  2002-03-05       Impact factor: 11.205

4.  Selectivity in an encapsulated cycloaddition reaction.

Authors:  Jian Chen; Julius Rebek
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

5.  Container molecules with portals: Reversibly switchable cycloalkane complexation.

Authors:  Thomas Gottschalk; Bernhard Jaun; François Diederich
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Molecular Recognition within a Self-Assembled Cylindrical Host.

Authors:  T Heinz; D M Rudkevich; J Rebek
Journal:  Angew Chem Int Ed Engl       Date:  1999       Impact factor: 15.336

7.  Guest-Controlled Formation of a Hydrogen-Bonded Molecular Capsule.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-10-04       Impact factor: 15.336

8.  An improved method for the study of reaction intermediates. The mechanism of peptide synthesis mediated by carbodiimides.

Authors:  J Rebek; D Fietler
Journal:  J Am Chem Soc       Date:  1973-06-13       Impact factor: 15.419

9.  Mechanism of the carbodiimide reaction. II. Peptide synthesis on the solid phase.

Authors:  J Rebek; D Feitler
Journal:  J Am Chem Soc       Date:  1974-03-06       Impact factor: 15.419

10.  Model studies in molecular recognition.

Authors:  J Rebek
Journal:  Science       Date:  1987-03-20       Impact factor: 47.728
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  9 in total

1.  Kinetic resolution of constitutional isomers controlled by selective protection inside a supramolecular nanocapsule.

Authors:  Simin Liu; Haiying Gan; Andrew T Hermann; Steven W Rick; Bruce C Gibb
Journal:  Nat Chem       Date:  2010-08-08       Impact factor: 24.427

2.  Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

Authors:  Per Restorp; Julius Rebek
Journal:  J Am Chem Soc       Date:  2008-08-13       Impact factor: 15.419

3.  Synthesis of a highly water-soluble derivative of amphotericin B with attenuated proinflammatory activity.

Authors:  Samusi A Adediran; Timothy P Day; Diptesh Sil; Matthew R Kimbrell; Hemamali J Warshakoon; Subbalakshmi S Malladi; Sunil A David
Journal:  Mol Pharm       Date:  2009 Sep-Oct       Impact factor: 4.939

4.  Gas Phase Ion Chemistry to Determine Isoaspartate in a Peptide Backbone.

Authors:  S T Ayrton; X Chen; R M Bain; C J Pulliam; M Achmatowicz; T G Flick; D Ren; R G Cooks
Journal:  J Am Soc Mass Spectrom       Date:  2018-03-15       Impact factor: 3.109

5.  Interaction energies and dynamics of acid-base pairs isolated in cavitands.

Authors:  Byron W Purse; Sara M Butterfield; Pablo Ballester; Alexander Shivanyuk; Julius Rebek
Journal:  J Org Chem       Date:  2008-08-02       Impact factor: 4.354

Review 6.  Chemistry and catalysis in functional cavitands.

Authors:  Richard J Hooley; Julius Rebek
Journal:  Chem Biol       Date:  2009-03-27

7.  Recognition of guests by water-stabilized cavitand hosts.

Authors:  Agustí Lledó; Richard J Hooley; Julius Rebek
Journal:  Org Lett       Date:  2008-07-26       Impact factor: 6.005

8.  Incubation of human sperm with micelles made from glycerophospholipid mixtures increases sperm motility and resistance to oxidative stress.

Authors:  Gonzalo Ferreira; Carlos Costa; Verónica Bassaizteguy; Marcelo Santos; Romina Cardozo; José Montes; Robert Settineri; Garth L Nicolson
Journal:  PLoS One       Date:  2018-06-01       Impact factor: 3.240

Review 9.  Applications of Nanoparticle-Antibody Conjugates in Immunoassays and Tumor Imaging.

Authors:  Xinhao Lin; André O'Reilly Beringhs; Xiuling Lu
Journal:  AAPS J       Date:  2021-03-14       Impact factor: 4.009
  9 in total

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