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Literature DB >> 21499500

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

M Elisa Juarez-Garcia¹, Shouyun Yu, Jeffrey W Bode.

Abstract

The design and general synthesis of enantiopure isoxazolidinone monomers as precursors for the preparation of enantiopure N-terminal hydroxylamine-β(3)-oligopeptides, which may be used as reaction partners with α-ketoacids in the decarboxylative amide ligation reaction, is described.

Entities: CellLine Chemical Gene Species

Year: 2010 PMID： 21499500 PMCID： PMC3074535 DOI： 10.1016/j.tet.2010.04.016

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

23 in total

Review 1. Synthesis of native proteins by chemical ligation.

Authors: P E Dawson; S B Kent
Journal: Annu Rev Biochem Date: 2000 Impact factor: 23.643

2. Chimeric (alpha/beta + alpha)-peptide ligands for the BH3-recognition cleft of Bcl-XL: critical role of the molecular scaffold in protein surface recognition.

Authors: Jack D Sadowsky; Margaret A Schmitt; Hee-Seung Lee; Naoki Umezawa; Shaomeng Wang; York Tomita; Samuel H Gellman
Journal: J Am Chem Soc Date: 2005-08-31 Impact factor: 15.419

3. Toward beta-amino acid proteins: a cooperatively folded beta-peptide quaternary structure.

Authors: Jade X Qiu; E James Petersson; Erin E Matthews; Alanna Schepartz
Journal: J Am Chem Soc Date: 2006-09-06 Impact factor: 15.419

Review 4. Evolving strategies for protein synthesis converge on native chemical ligation.

Authors: Derek Macmillan
Journal: Angew Chem Int Ed Engl Date: 2006-11-27 Impact factor: 15.336

Review 5. The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.

Authors: Dieter Seebach; Albert K Beck; Daniel J Bierbaum
Journal: Chem Biodivers Date: 2004-08 Impact factor: 2.408

6. Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids.

Authors: Ismail Ibrahem; Ramon Rios; Jan Vesely; Gui-Ling Zhao; Armando Córdova
Journal: Chem Commun (Camb) Date: 2006-11-23 Impact factor: 6.222

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

Authors: Nancy Carrillo; Eric A Davalos; Justin A Russak; Jeffrey W Bode
Journal: J Am Chem Soc Date: 2006-02-08 Impact factor: 15.419

8. Toward beta-amino acid proteins: design, synthesis, and characterization of a fifteen kilodalton beta-peptide tetramer.

Authors: E James Petersson; Alanna Schepartz
Journal: J Am Chem Soc Date: 2008-01-01 Impact factor: 15.419

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

Review 1. Synthesis of native proteins by chemical ligation.

2. Chimeric (alpha/beta + alpha)-peptide ligands for the BH3-recognition cleft of Bcl-XL: critical role of the molecular scaffold in protein surface recognition.

3. Toward beta-amino acid proteins: a cooperatively folded beta-peptide quaternary structure.

Review 4. Evolving strategies for protein synthesis converge on native chemical ligation.

Review 5. The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.

6. Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids.

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

8. Toward beta-amino acid proteins: design, synthesis, and characterization of a fifteen kilodalton beta-peptide tetramer.

9. A concise approach to structurally diverse beta-amino acids.

10. Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide alpha-ketoacids.

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

2. Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation.

3. Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate.