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Literature DB >> 18855357

Oxo-ester mediated native chemical ligation: concept and applications.

Qian Wan¹, Jin Chen, Yu Yuan, Samuel J Danishefsky.

Abstract

A direct oxo-ester peptide ligation method has been developed. Through the use of an activated C-terminal para nitrophenyl ester (1), it is possible to achieve direct cysteine ligations (1 + 2 --> 4). Peptide substrates incorporating bulky C-terminal amino acids (1) can be accommodated with high reaction efficiency.

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Esters
Erythropoietin

Year: 2008 PMID： 18855357 PMCID： PMC2645925 DOI： 10.1021/ja804993y

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

20 in total

1. Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology.

Authors: T M Hackeng; J H Griffin; P E Dawson
Journal: Proc Natl Acad Sci U S A Date: 1999-08-31 Impact factor: 11.205

2. 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

3. Development of efficient methods for accomplishing cysteine-free peptide and glycopeptide coupling.

Authors: Gong Chen; Qian Wan; Zhongping Tan; Cindy Kan; Zihao Hua; Krishnakumar Ranganathan; Samuel J Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Native chemical ligation at valine.

Authors: Christian Haase; Heike Rohde; Oliver Seitz
Journal: Angew Chem Int Ed Engl Date: 2008 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. Cysteine-free peptide and glycopeptide ligation by direct aminolysis.

Authors: Richard J Payne; Simon Ficht; William A Greenberg; Chi-Huey Wong
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. Mechanistic studies of peptide oxazolone racemization.

Authors: M Goodman; W J McGahren
Journal: Tetrahedron Date: 1967-05 Impact factor: 2.457

8. 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

9. 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

10. Methionine ligation strategy in the biomimetic synthesis of parathyroid hormones.

Authors: J P Tam; Q Yu
Journal: Biopolymers Date: 1998-10-15 Impact factor: 2.505

14 in total

1. 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

Review 2. Toward fully synthetic, homogeneous glycoproteins: advances in chemical ligation.

Authors: Yu Yuan; Jin Chen; Qian Wan; Rebecca M Wilson; Samuel J Danishefsky
Journal: Biopolymers Date: 2010 Impact factor: 2.505

3. 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

Review 4. 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

5. A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides.

Authors: Jin Chen; Ping Wang; Jianglong Zhu; Qian Wan; Samuel J Danishefsky
Journal: Tetrahedron Date: 2010-03-27 Impact factor: 2.457

6. Biofabrication of reinforced 3D-scaffolds using two-component hydrogels.

Authors: Kristel W M Boere; Maarten M Blokzijl; Jetze Visser; J Elder A Linssen; Jos Malda; Wim E Hennink; Tina Vermonden
Journal: J Mater Chem B Date: 2015-10-19 Impact factor: 6.331

7. Hydrogels Formed by Oxo-ester Mediated Native Chemical Ligation.

Authors: Iossif Strehin; Dmitri Gourevitch; Yong Zhang; Ellen Heber-Katz; Phillip B Messersmith
Journal: Biomater Sci Date: 2013-06-01 Impact factor: 6.843

8. Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.

Authors: Pavel Nagorny; Bernhard Fasching; Xuechen Li; Gong Chen; Baptiste Aussedat; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2009-04-29 Impact factor: 15.419

9. Toward homogeneous erythropoietin: chemical synthesis of the Ala1-Gly28 glycopeptide domain by "alanine" ligation.

Authors: Cindy Kan; John D Trzupek; Bin Wu; Qian Wan; Gong Chen; Zhongping Tan; Yu Yuan; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2009-04-22 Impact factor: 15.419

10. A general strategy for the preparation of C-terminal peptide alpha-ketoacids by solid phase peptide synthesis.

Authors: Lei Ju; Jeffrey W Bode
Journal: Org Biomol Chem Date: 2009-04-02 Impact factor: 3.876