Literature DB >> 23821753

Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

Ting Wang1, Samuel J Danishefsky.   

Abstract

The synthesis of polypeptides on solid phase via mediation by isonitriles is described. The acyl donor is a thioacid, which presumably reacts with the isonitrile to generate a thio-formimidate carboxylate mixed anhydride intermediate. Applications of this chemistry to reiterative solid-phase peptide synthesis as well as solid-phase fragment coupling are described.

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Year:  2013        PMID： 23821753      PMCID： PMC3718127          DOI： 10.1073/pnas.1310431110

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


  34 in total

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Journal:  Trends Biotechnol       Date:  2000-06       Impact factor: 19.536

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Authors:  Xiangyang Wu; Jennifer L Stockdill; Peter K Park; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

3.  Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

Authors:  Per Restorp; Julius Rebek
Journal:  J Am Chem Soc       Date:  2008-08-13       Impact factor: 15.419

4.  Fragment condensation of C-terminal pseudoproline peptides without racemization on the solid phase.

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Review 5.  Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids.

Authors:  G B Fields; R L Noble
Journal:  Int J Pept Protein Res       Date:  1990-03

6.  Thio-mediated synthesis of derivatized N-linked glycopeptides using isonitrile chemistry.

Authors:  Xiangyang Wu; Yu Yuan; Xuechen Li; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-08-12       Impact factor: 2.415

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8.  Addressing mechanistic issues in the coupling of isonitriles and carboxylic acids: potential routes to peptidic constructs.

Authors:  Xuechen Li; Yu Yuan; Cindy Kan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419

9.  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

Review 10.  Oxytocin, vasopressin, and human social behavior.

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2.  Erythropoietin derived by chemical synthesis.

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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.  Combining triazole ligation and enzymatic glycosylation on solid phase simplifies the synthesis of very long glycoprotein analogues.

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Journal:  Chem Sci       Date:  2015-04-14       Impact factor: 9.825

5.  Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.

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  5 in total

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