Literature DB >> 19334683

Toward homogeneous erythropoietin: non-NCL-based chemical synthesis of the Gln78-Arg166 glycopeptide domain.

Zhongping Tan1, Shiying Shang, Tamara Halkina, Yu Yuan, Samuel J Danishefsky.   

Abstract

Single erythropoietin (EPO) glycoforms with defined mature oligosaccharide structures and amino acid sequences are essential to elucidate the molecular mechanisms by which carbohydrates exert various physiological and metabolic functions and to explore the possible links between carbohydrates and the prevention or management of diseases. To demonstrate that it is possible to generate EPO even without recourse to cysteine-based native chemical ligation, a concise synthesis of the partially protected EPO fragment (78-166) bearing fully mature N- and O-glycans is described.

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Year:  2009        PMID: 19334683      PMCID: PMC2765484          DOI: 10.1021/ja808704m

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


  27 in total

1.  Extending synthetic access to proteins with a removable acyl transfer auxiliary.

Authors:  John Offer; C N C Boddy; Philip E Dawson
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

Review 2.  Protein N-glycosylation along the secretory pathway: relationship to organelle topography and function, protein quality control, and cell interactions.

Authors:  Jürgen Roth
Journal:  Chem Rev       Date:  2002-02       Impact factor: 60.622

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.  The impact of glycosylation on the biological function and structure of human immunoglobulins.

Authors:  James N Arnold; Mark R Wormald; Robert B Sim; Pauline M Rudd; Raymond A Dwek
Journal:  Annu Rev Immunol       Date:  2007       Impact factor: 28.527

5.  Efficient synthesis and comparative studies of the arginine and Nomega,Nomega-dimethylarginine forms of the human nucleolin glycine/arginine rich domain.

Authors:  Sotir Zahariev; Corrado Guarnaccia; Francesco Zanuttin; Alessandro Pintar; Gennaro Esposito; Gordana Maravić; Bernard Krust; Ara G Hovanessian; Sándor Pongor
Journal:  J Pept Sci       Date:  2005-01       Impact factor: 1.905

Review 6.  Synthetic carbohydrate-based antitumor vaccines: challenges and opportunities.

Authors:  Ouathek Ouerfelli; J David Warren; Rebecca M Wilson; Samuel J Danishefsky
Journal:  Expert Rev Vaccines       Date:  2005-10       Impact factor: 5.217

7.  Application of Fmoc-amino acid carrying an unmasked carbohydrate to the synthesis of the epidermal growth factor-like domain of bovine blood coagulation factor IX.

Authors:  Toshio Takemura; Hironobu Hojo; Yoshiaki Nakahara; Takeshi Ishimizu; Sumihiro Hase
Journal:  Org Biomol Chem       Date:  2003-11-24       Impact factor: 3.876

Review 8.  Molecular biology of erythropoietin.

Authors:  Wolfgang Jelkmann
Journal:  Intern Med       Date:  2004-08       Impact factor: 1.271

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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  25 in total

Review 1.  Emerging technologies for making glycan-defined glycoproteins.

Authors:  Lai-Xi Wang; Joseph V Lomino
Journal:  ACS Chem Biol       Date:  2011-12-14       Impact factor: 5.100

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

Authors:  Ping Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-11-04       Impact factor: 15.419

3.  On-resin convergent synthesis of a glycopeptide from HIV gp120 containing a high mannose type N-linked oligosaccharide.

Authors:  Rui Chen; Thomas J Tolbert
Journal:  Methods Mol Biol       Date:  2011

4.  Rational development of a strategy for modifying the aggregatibility of proteins.

Authors:  Zhongping Tan; Shiying Shang; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-28       Impact factor: 11.205

5.  Insights into the finer issues of native chemical ligation: an approach to cascade ligations.

Authors:  Zhongping Tan; Shiying Shang; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

6.  Encouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides.

Authors:  Ping Wang; Xuechen Li; Jianglong Zhu; Jin Chen; Yu Yuan; Xiangyang Wu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2011-01-05       Impact factor: 15.419

7.  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

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.  Total synthesis of the 2,6-sialylated immunoglobulin G glycopeptide fragment in homogeneous form.

Authors:  Ping Wang; Jianglong Zhu; Yu Yuan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

Review 10.  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

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