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Literature DB >> 16448107

Iterative, aqueous synthesis of beta3-oligopeptides without coupling reagents.

Nancy Carrillo¹, Eric A Davalos, Justin A Russak, Jeffrey W Bode.

Abstract

The chemoselective synthesis of amides by decarboxylative couplings of alpha-ketoacids and isoxazolidines makes possible an iterative approach to poly-beta3-peptides. Peptide assembly occurs under aqueous conditions and requires no coupling reagents. The requisite isoxazolidine monomers are prepared in enantiopure form by a convenient two-step protocol starting from the appropriate aldehydes.

Entities: Chemical Gene

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Year: 2006 PMID： 16448107 DOI： 10.1021/ja057706j

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

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Cited

15 in total

Review 1. Foldamers as versatile frameworks for the design and evolution of function.

Authors: Catherine M Goodman; Sungwook Choi; Scott Shandler; William F DeGrado
Journal: Nat Chem Biol Date: 2007-05 Impact factor: 15.040

2. Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.

Authors: Aaron M Dumas; Gary A Molander; Jeffrey W Bode
Journal: Angew Chem Int Ed Engl Date: 2012-04-26 Impact factor: 15.336

3. Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β-oligopeptides by chemoselective amide ligation.

Authors: M Elisa Juarez-Garcia; Shouyun Yu; Jeffrey W Bode
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

10. Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.

Authors: Jessica P Shackleford; Bo Shen; Jeffrey N Johnston
Journal: Proc Natl Acad Sci U S A Date: 2011-12-19 Impact factor: 11.205

Iterative, aqueous synthesis of beta3-oligopeptides without coupling reagents.

Review 1. Foldamers as versatile frameworks for the design and evolution of function.

2. Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.

3. Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β-oligopeptides by chemoselective amide ligation.

4. Promising general solution to the problem of ligating peptides and glycopeptides.

5. Chemoselective protection of alpha-ketoacids by direct annulations with oximes.

6. Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

7. Drug discovery: Combichem all over again.

8. Public libraries.

9. Synthetic fermentation of bioactive non-ribosomal peptides without organisms, enzymes or reagents.

10. Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.