Literature DB >> 23775885

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

Rebecca M Wilson1, Suwei Dong, Ping Wang, Samuel J Danishefsky.   

Abstract

The total synthesis of a homogeneous erythropoietin (EPO), possessing the native amino acid sequence and chitobiose glycans at each of the three wild-type sites of N glycosylation, has been accomplished in our laboratory. We provide herein an account of our decade-long research effort en route to this formidable target compound. The optimization of the synergy of the two bedrock sciences we now call biology and chemistry was central to the success of the synthesis of EPO.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amino acids; erythropoietin; glycoprotein; synthetic methods; total synthesis

Mesh:

Substances:

Year:  2013        PMID: 23775885      PMCID: PMC4729195          DOI: 10.1002/anie.201301666

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  65 in total

1.  Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo.

Authors:  Izumi Sakamoto; Katsunari Tezuka; Kazuhiro Fukae; Kazuyuki Ishii; Keisuke Taduru; Masatoshi Maeda; Masaki Ouchi; Kenta Yoshida; Yuri Nambu; Jun Igarashi; Naohiro Hayashi; Takashi Tsuji; Yasuhiro Kajihara
Journal:  J Am Chem Soc       Date:  2012-03-15       Impact factor: 15.419

2.  Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone.

Authors:  Baptiste Aussedat; Bernhard Fasching; Eric Johnston; Neeraj Sane; Pavel Nagorny; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-02-06       Impact factor: 15.419

Review 3.  On the remarkable antitumor properties of fludelone: how we got there.

Authors:  Alexey Rivkin; Ting-Chao Chou; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-06       Impact factor: 15.336

4.  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

5.  Native chemical ligation at valine: a contribution to peptide and glycopeptide synthesis.

Authors:  Jin Chen; Qian Wan; Yu Yuan; Jianglong Zhu; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  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

7.  An advance in proline ligation.

Authors:  Shiying Shang; Zhongping Tan; Suwei Dong; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2011-06-23       Impact factor: 15.419

8.  Toward Homogeneous Erythropoietin: Application of Metal Free Dethiylation in the Chemical Synthesis of the Ala79-Arg166 Glycopeptide Domain.

Authors:  Suwei Dong; Shiying Shang; Zhongping Tan; Samuel J Danishefsky
Journal:  Isr J Chem       Date:  2011-11       Impact factor: 3.333

9.  Mature Homogeneous Erythropoietin-Level Building Blocks by Chemical Synthesis: The EPO 114-166 Glycopeptide Domain, Presenting the O-Linked Glycophorin.

Authors:  Jiehao Chen; Gong Chen; Bin Wu; Qian Wan; Zhongping Tan; Zihao Hua; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2006-11-13       Impact factor: 2.415

10.  Chemical synthesis of a glycoprotein having an intact human complex-type sialyloligosaccharide under the Boc and Fmoc synthetic strategies.

Authors:  Naoki Yamamoto; Yasutaka Tanabe; Ryo Okamoto; Philip E Dawson; Yasuhiro Kajihara
Journal:  J Am Chem Soc       Date:  2007-12-18       Impact factor: 15.419

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  15 in total

Review 1.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

Review 2.  Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins.

Authors:  Somasekhar Bondalapati; Muhammad Jbara; Ashraf Brik
Journal:  Nat Chem       Date:  2016-04-22       Impact factor: 24.427

3.  Chemical biology of glycoproteins: From chemical synthesis to biological impact.

Authors:  Yaohao Li; Amy H Tran; Samuel J Danishefsky; Zhongping Tan
Journal:  Methods Enzymol       Date:  2019-03-14       Impact factor: 1.600

4.  Erythropoietin derived by chemical synthesis.

Authors:  Ping Wang; Suwei Dong; Jae-Hung Shieh; Elizabeth Peguero; Ronald Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal:  Science       Date:  2013-12-13       Impact factor: 47.728

5.  Chemoenzymatic Synthesis of HIV-1 Glycopeptide Antigens.

Authors:  Guanghui Zong; Chao Li; Lai-Xi Wang
Journal:  Methods Mol Biol       Date:  2020

6.  A Helping Hand to Overcome Solubility Challenges in Chemical Protein Synthesis.

Authors:  Michael T Jacobsen; Mark E Petersen; Xiang Ye; Mathieu Galibert; George H Lorimer; Vincent Aucagne; Michael S Kay
Journal:  J Am Chem Soc       Date:  2016-09-01       Impact factor: 15.419

7.  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

Review 8.  Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions.

Authors:  Lai-Xi Wang; Mohammed N Amin
Journal:  Chem Biol       Date:  2014-01-16

Review 9.  Chemoenzymatic Methods for the Synthesis of Glycoproteins.

Authors:  Chao Li; Lai-Xi Wang
Journal:  Chem Rev       Date:  2018-08-24       Impact factor: 60.622

10.  Synthesis of granulocyte-macrophage colony-stimulating factor as homogeneous glycoforms and early comparisons with yeast cell-derived material.

Authors:  Qiang Zhang; Eric V Johnston; Jae-Hung Shieh; Malcolm A S Moore; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2014-02-10       Impact factor: 11.205

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