Literature DB >> 22499784

Probing the stability of nonglycosylated wild-type erythropoietin protein via reiterative alanine ligations.

John A Brailsford1, Samuel J Danishefsky.   

Abstract

Nonglycosylated erythropoietin bearing acetamidomethyl protecting groups at the cysteine residues has been synthesized via chemical methods. Alanine ligation was used to assemble four peptide fragments, themselves prepared by solid phase peptide synthesis. This work outlines a route for the synthesis of homogeneous glycosylated erythropoietin.

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Year:  2012        PMID: 22499784      PMCID: PMC3358843          DOI: 10.1073/pnas.1202762109

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  27 in total

1.  Covalent capture: a new tool for the purification of synthetic and recombinant polypeptides.

Authors:  M Villain; J Vizzavona; K Rose
Journal:  Chem Biol       Date:  2001-07

2.  A one-pot total synthesis of crambin.

Authors:  Duhee Bang; Stephen B H Kent
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-03       Impact factor: 15.336

3.  Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides.

Authors:  Qian Wan; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  Glycoprotein synthesis: an update.

Authors:  David P Gamblin; Eoin M Scanlan; Benjamin G Davis
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

5.  Design and synthesis of a homogeneous erythropoietin analogue with two human complex-type sialyloligosaccharides: combined use of chemical and bacterial protein expression methods.

Authors:  Kiriko Hirano; Derek Macmillan; Katsunari Tezuka; Takashi Tsuji; Yasuhiro Kajihara
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Recent Departures in the Synthesis of Peptides and Glycopeptides.

Authors:  Cindy Kan; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2009-11-07       Impact factor: 2.457

7.  Selective desulfurization of cysteine in the presence of Cys(Acm) in polypeptides obtained by native chemical ligation.

Authors:  Brad L Pentelute; Stephen B H Kent
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005

8.  Structural characterization of natural human urinary and recombinant DNA-derived erythropoietin. Identification of des-arginine 166 erythropoietin.

Authors:  M A Recny; H A Scoble; Y Kim
Journal:  J Biol Chem       Date:  1987-12-15       Impact factor: 5.157

9.  Powerful solvent systems useful for synthesis of sparingly-soluble peptides in solution.

Authors:  H Kuroda; Y N Chen; T Kimura; S Sakakibara
Journal:  Int J Pept Protein Res       Date:  1992 Sep-Oct

10.  Structural characterization of human erythropoietin.

Authors:  P H Lai; R Everett; F F Wang; T Arakawa; E Goldwasser
Journal:  J Biol Chem       Date:  1986-03-05       Impact factor: 5.157

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  9 in total

1.  From EPOthilone to EPO: Aa challenge for natural product synthesis.

Authors:  Zachary Z Brown; Tom W Muir
Journal:  Proc Natl Acad Sci U S A       Date:  2012-04-23       Impact factor: 11.205

2.  Engineering of therapeutic polypeptides through chemical synthesis: early lessons from human parathyroid hormone and analogues.

Authors:  Suwei Dong; Shiying Shang; Jianfeng Li; Zhongping Tan; Thomas Dean; Akira Maeda; Thomas J Gardella; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-08-29       Impact factor: 15.419

3.  Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors:  Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2015-10-01       Impact factor: 15.419

4.  At last: erythropoietin as a single glycoform.

Authors:  Ping Wang; Suwei Dong; John A Brailsford; Karthik Iyer; Steven D Townsend; Qiang Zhang; Ronald C Hendrickson; JaeHung Shieh; Malcolm A S Moore; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

5.  An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation.

Authors:  Ping Wang; Baptiste Aussedat; Yusufbhai Vohra; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

Review 6.  Total synthesis of glycosylated proteins.

Authors:  Alberto Fernández-Tejada; John Brailsford; Qiang Zhang; Jae-Hung Shieh; Malcolm A S Moore; Samuel J Danishefsky
Journal:  Top Curr Chem       Date:  2015

Review 7.  The winding pathway to erythropoietin along the chemistry-biology frontier: a success at last.

Authors:  Rebecca M Wilson; Suwei Dong; Ping Wang; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-17       Impact factor: 15.336

8.  Revisiting oxytocin through the medium of isonitriles.

Authors:  Ting Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-08-02       Impact factor: 15.419

9.  Cysteine promoted C-terminal hydrazinolysis of native peptides and proteins.

Authors:  Anna L Adams; Ben Cowper; Rachel E Morgan; Bhavesh Premdjee; Stephen Caddick; Derek Macmillan
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-09       Impact factor: 15.336

  9 in total

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